Category: 344-14-9

Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 344-14-9, Safety of Dimethyl 2-fluoromalonate

Example 1; Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10b) 23.01 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (9) over 3 minutes while keeping the internal temperature between 25 C. and 30 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo[3.1.0]hex-2-ene (8) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent: toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of Formula 10a and the compound of Formula lab as a yellow oily material.1H NMR (500 MHz, DMSO-d6): delta 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H).13C NMR (125 MHz, DMSO-d6) delta 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125-59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6); delta -172.43, -172.36. HRMS (ES) m/z:[M+Na]+ calcd for C10H13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1060, 1031, 936, 838, 787, 722, 668, 415 cm-1,

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2011/65934; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 344-14-9, Safety of Dimethyl 2-fluoromalonate

Example 1; Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (10b) 23.01 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (9) over 3 minutes while keeping the internal temperature between 25 C. and 30 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo[3.1.0]hex-2-ene (8) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent: toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of Formula 10a and the compound of Formula lab as a yellow oily material.1H NMR (500 MHz, DMSO-d6): delta 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H).13C NMR (125 MHz, DMSO-d6) delta 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125-59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6); delta -172.43, -172.36. HRMS (ES) m/z:[M+Na]+ calcd for C10H13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1060, 1031, 936, 838, 787, 722, 668, 415 cm-1,

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2011/65934; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 344-14-9, name is Dimethyl 2-fluoromalonate, A new synthetic method of this compound is introduced below., Recommanded Product: Dimethyl 2-fluoromalonate

Sodium hydride (60% dispersion in mineral oil; 2.93 g, 73.3 mmol) was added to a solution of dimethyl 2-fluoromalonate (10.0 g, 66.6 mmol) in THF (218 mL) with vigorous stirring. After 30 minutes iodomethane (4.56 mL, 73.3 mmol) was added. The reaction was stirred for a further 3 hours. The reaction was quenched with water and then extracted with EtOAc (4*100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford dimethyl 2-fluoro-2-methyl-propanedioate (8.4 g, 77%) as an orange oil. 1H NMR (300 MHz, DMSO-d6, 27 C.) 1.72 (3H, d), 3.77 (6H, s).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AstraZeneca AB; BARLAAM, Bernard Christophe; O’DONOVAN, Daniel Hillebrand; HUGHES, Samantha Jayne; MOSS, Thomas Andrew; NISSINK, Johannes Wilhelmus Maria; SCOTT, James Stewart; YANG, Bin; (148 pag.)US2018/111931; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2-fluoromalonate, its application will become more common.

Reference:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 344-14-9, name is Dimethyl 2-fluoromalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 344-14-9, HPLC of Formula: C5H7FO4

General procedure: The solution of 25% NaOMe in methanol (10.28 g, 190.38 mmol) was diluted with methanol(50 ml) under N2 atm and cooled to 0 0C. To this, compound 1a (14.90 g, 95.19 mmol) followedby compound 6 (10 g, 105.77 mmol) were added and stirred the reaction mixture at roomtemperature for 16 h. The progress of the reaction was monitored by TLC (10% Ethyl acetatein petroleum ether) showed completion of the reaction. After completion of the reaction; thereaction mixture was evaporated and solid was dissolved in H2O and acidified with Conc.HCl(~ pH 2), to give the white solid. The resulting solid was filtered and washed with water anddried under vacuum give the pure compound 7a (10 g; 48.78 mmol, 72%) as an off white solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sambaiah; Mallesham, Poosa; Shiva Kumar; Bobde, Yamini; Hota, Prasanta Kumar; Yennam, Satyanarayana; Ghosh, Balaram; Behera, Manoranjan; Synlett; vol. 30; 5; (2019); p. 586 – 592;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 344-14-9 as follows. Application In Synthesis of Dimethyl 2-fluoromalonate

A mixture of 2-fluoro-4-amidinopyridine hydrochloride (1.17 g, 6.662 mmol), dimethyl fluoromalonate (1 g, 6.662 mmol), DBU (3.35 mL, 22.4 mmol) and MeOH (50 mL) was stirred at room temperature overnight. The crude reaction mixture was evaporated under reduced pressure to yield a brown oil. A 2 N HC1 solution was cautiously added and the precipitate was collected by filtration, washed with water and dried in a vacuum oven to give the title compound (0.992 g, 66% yield). LCMS: RT 2.91 min, MI 225, Method (4LCMS1).

According to the analysis of related databases, 344-14-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 344-14-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 344-14-9, name is Dimethyl 2-fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows.

In a dry argon-protected reaction tube, 4.0 mol% of [Pd(C3H5)Cl]2, 8.0 mol% was added successively.The mixture was stirred at room temperature for 30 minutes, then 1.0 equiv. 5 (0.2 mmol) was added and stirring was continued for 10 minutes. 3.0 equiv. 8 (1.5 mmol) and 3.0 equiv. of Base (1.5 mmol) were added to the reaction tube and the reaction was stirred. After the reaction is completed, the solvent is removed under reduced pressure and the residue is subjected to a thin layer chromatography to give the desired product (petroleum ether/dichloromethane = 1/1, or petroleum ether/ethyl acetate = 10/1, v/v).

The chemical industry reduces the impact on the environment during synthesis Dimethyl 2-fluoromalonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Tongji University; Zhao Xiaoming; Gao Ning; Cai Chengsi; Cai Juewang; (20 pag.)CN104926720; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Part A: 5-Fluoro-4,6-dihydroxy-2-methylpyrimidine A solution of 200 ml. of 25% wt sodium methoxide in methanol (0.84 mol) was diluted with an additional 200 ml. of methanol. Acetamidine-HCI (40 g , 0.42 mol) was added to the sodium methoxide solution (white precipitate formed), followed by addition of dimethyl fluoromalonate (70 g, 0.46 mol). The contents were stirred at room temperature overnight, then concentrated in vacuo to dryness. The resulting residue was redissolved in hot water (300 ml_). After cooling the aqueous solution to room temperature, concentrated HCI was added slowly until crystal formation (fine white prisms) took place at about pH 5. Concentrated HCI was added dropwise until pH 3, and then the contents were filtered. The isolated crystals were rinsed with 1 M HCI and dried under vacuum to provide 5-fluoro-4,6-dihydroxy-2-methylpyrimidine (65.5 g, >100%). LCMS: (M+H)+: 145.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO. 2) LIMITED; AUBART, Kelly, Marshall; GILLIAN, Jason, Michael; QIN, Donghui; MCKEOWN, Robert, Rahn; WILLIAMS, Glenn, R.; WO2013/82388; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 344-14-9, A common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: In a 50 mL two-necked flask containing dichloromethane (10 mL) were added the amine (17 mmol) followed by the aldehyde (15 mmol) and the resulting reaction mixture was allowed to stir at rt for 2 h, before the fluorinated dicarbonyl system (10 mmol) was added. The reaction mixture was stirred at rt for 16 h, evaporated and the residue dissolved in dichloromethane (20 mL), washed with distilled water (2×20 mL), dried over magnesium sulfate and evaporated, to give the desired product. Further purification by distillation or column chromatography eluting from hexane/ethyl acetate was carried out when appropriate. Analytical and spectroscopic data for each individual compound are listed below. For NMR data only resonances of one diastereoisomer or conformer is given for clarity.

The synthetic route of 344-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lisse, Etienne; Sandford, Graham; Journal of Fluorine Chemistry; vol. 206; (2018); p. 117 – 124;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 344-14-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

First, put a stirrer in a 35 mL sealed tube, and then add 2-methyl-1-butene-3-yne (32 muL, 0.33 mmol), 0.9 mL tetrahydrofuran (0.9 mL), and 2-chloroacetamido Quinoline (66.2mg, 0.3mmol), dimethyl 2-fluoromalonate (70.4mg, 0.45mmol), to this mixed solution were added CuI (5.7mg, 0.03mmol) and Cs2CO3 (117.3mg, 0.36mmol), charge N2 for 3 minutes with a glass tube connected to nitrogen, fully drive out the air, seal the nozzle with a cock, and stir the reaction at 800C for 1.5 hours. After the reaction is completed, the system is cooled to room temperature and added to the reaction system. 2ml of distilled water was extracted with ethyl acetate. The organic phases were combined, and the solvent of the organic phase was distilled off under reduced pressure. 84.1 mg of product 4e was separated by silica gel column chromatography. The yield was 70%.

The synthetic route of Dimethyl 2-fluoromalonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anyang Normal University; Lv Yunhe; Pu Weiya; Wang Xin; Wang Xiaoxing; (15 pag.)CN110627718; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics