Month: September 2021

Application of 62638-06-6, 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. 62638-06-6, name is Dimethyl cyclohexane-1,3-dicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 25; l,3-Dicarbomethoxybicyclo[3.2.1]octane; A cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (60mL) in a 3-neck 500mL round bottom flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol) at a rate to keep the pot temperature <-50C, warmed to 0C for 5 minutes, then recooled (-67 C). l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (DMPU, 36.3mL, 300 mmole, dried over molecular seives) was added dropwise so as to keep pot temp < -60 C, then a solution of dimethyl cyclohexane-l,3-dicarboxylate (12.01g, 60 mmol) in anhydrous THF (20mL) was likewise added dropwise. After lh at -67 C, a solution of l-bromo-2-chloroethane (12.05g, 84 mmol) in anhydrous THF (15mL) was added dropwise so as to keep pot temp <-50 C, and the mixture was warmed to room temperature over 1.5h and stirred at room temperature for 18h, then cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford 15.36g (97% of theoretical) of a pale yellow oil which was essentially the desired intermediate with minor impurities.A solution of l-(2-chloroethyl)-l,3-dicarbomethoxycyclohexane (all of semi-purified from 60 mmol dimethyl cyclohexane-l,3-dicarboxylate) and DMPU (36.3mL, 300 mmol) in anhydrous THF (150mL) under nitrogen in a 500mL 3-neck flask equipped with magnetic stirring, addition funnel, and gas inlet/thermometer was cooled to -67C. Meanwhile, a cooled (-67C) solution of dry diisopropylamine (ll.OmL, 78 mmol) in anhydrous THF (75mL) under nitrogen was treated via syringe with 2.4N n-butyllithium/hexane (30mL, 72 mmol), the mixture was warmed to 0C for 5 min, then recooled (-67C). The LDA solution was cannulated in portions (~6) into the other solution at a rate to keep pot temperature <-60 C, then the mixture was stirred at -67 C for 30 min, warmed to room temperature over 1.5h, then stirred at room temperature for 18h,. cooled on an ice bath and quenched with saturated aqueous ammonium chloride (50mL). The organic solvent was removed in vacuo and the aqueous residue was extracted with 9:1 hexane/ethyl acetate (150mL, lOOmL, 2X50mL). The combined organic extracts were washed with water (lOOmL), dried (MgS04), and concentrated in vacuo. The residue was dissolved in methylene chloride and passed through a pad of alumina in a 60mL fritted glass funnel (eluted with methylene chloride) to afford crude subject material (9.52g) as a pale yellow oil. Chromatography on silica gel (~400cc) eluted with 40%, then 50% methylene chloride/hexane, then methylene chloride alone, then 10% ethyl acetate/methylene chloride afforded 8.32g (61% for two steps from dimethyl cyclohexane-l,3-dicarboxylate) purified subject material as a very pale yellow oil. [M+H]+=226.9. *H NMR (CDC13) 8 3.66 (s,6H), 2.20-2.30 (m,lH), 2.00-2.10 (m,2H), 1.70-1.80 (m,5H), 1.55-1.65 (m,4H). 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 cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see. Reference:
Patent; ROYALTY, Susan Marie; BURNS, James Ford; SCICINSKI, Jan Jozef; JAGDMANN, JR., Gunnar Erik; FOGLESONG, Robert James; GRIFFIN, Kellee Renee; DYAKONOV, Tatyana; MIDDLEMISS, David; WO2006/12395; (2006); A2;,
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Application of 1459-96-7, These common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, 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.

Example 81 Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV) A mixture of Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester (III, Example 80, 20.4 g, 89.5 mmol), barium hydroxide octahydrate (14 g, 44.7 mmol) in methanol (160 ml) and water (40 ml) is stirred at 20-25 C. for 18 hour. The mixture is diluted with water (600 ml) and extracted with hexane (150 ml*2). The aqueous mixture is acidified (6 N hydrochloric acid) to pH=1-2 and extracted with chloroform (150 ml*2). The combined chloroform extracts are concentrated. The residue is dissolved in toluene, filtered and concentrated to give the title compound, mp=169-173 C.

The synthetic route of 1459-96-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biogen, Inc.; US6649600; (2003); B1;,
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Reference of 15964-79-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15964-79-1 name is Methyl 2-(3,4-dimethoxyphenyl)acetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a 1.0 L three-necked round-bottomed flask was added 50 mL of THF and the reaction mixture was cooled to -78 C. Butyl lithium (BuLi, 1.6 M, 14.4 mL, 23 mmol) was added dropwise keeping the temperature below -70 C. Acetonitrile (1.3 mL, 25 mmol) in 30 mL of THF was added dropwise to the flask amidst stirring and cooling. After 2 hours (h) of stirring, (3,4-dimethoxyphenyl)acetic acid methyl ester (2.3 g, 11 mmol) was added to the resulting white colloidal mixture in the flask. The reaction mixture was stirred for a further 2 h, followed by the addition of saturated ammonium chloride solution (NH4Cl, 75 mL) at -78 C. The organic layer was separated, dried with sodium sulfate (Na2SO4), filtered to remove the drying agent and evaporated to dryness to give the crude product. This crude product was purified by silica gel column chromatography, eluting with 30-70% ethyl acetate (EtOAc) in hexanes to yield 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile in the form of a solidifying amber oil, 1.8 g (75%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Cole, Derek Cecil; Boschelli, Diane Harris; Wang, Yanong Daniel; Asselin, Magda; Joseph-McCarthy, Diane Marie; Prashad, Amarnauth Shastrie; Wissner, Allan; Dushin, Russell; Wu, Biqi; Tumey, Lawrence Nathan; Niu, Chuan S.; Chen, Joan; US2007/287708; (2007); A1;,
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Synthetic Route of 3044-06-2, The chemical industry reduces the impact on the environment during synthesis 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, I believe this compound will play a more active role in future production and life.

General procedure: Diethyl ethoxymethylenemalonate (4.6mmol) were add to a solution of sodium hydride (9.7mmol) and compound 14a-l (4.2mmol) in ethanol (20mL), the reaction mixture was stirred at 80C for 2h. After the reaction completed, the mixture was added 10mL 6M hydrochloric acid and stirred for 0.5h, then the precipitate was collected by filtration. The resulting residue was recrystallized from ethanol to yield ethyl 2-(4-alkoxyphenyl-3-cyano)-6-oxo-1,6-dihydropyrimidine-5-carboxylate(15a-l).

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, Diethyl 2-(1-ethoxyethylidene)malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mao, Qing; Dai; Xu, Gaoyang; Su, Yu; Zhang, Bing; Liu, Dan; Wang, Shaojie; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 62638-06-6, name is Dimethyl cyclohexane-1,3-dicarboxylate, 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 62638-06-6, Quality Control of Dimethyl cyclohexane-1,3-dicarboxylate

REFERENCE EXAMPLE 72 Monomethyl 1,3-cyclohexanedicarboxylate In 85 ml of methanol were dissolved 8.33 g of dimethyl 1,3-cyclohexanedicarboxylate, and 41.6 ml of 1N aqueous sodium hydroxide solution was added thereto, and the resulting mixture was stirred at room temperature for 4 hours. The solvent was distilled off under reduced pressure and the aqueous solution was washed with ethyl acetate. The pH was adjusted to 1 with diluted hydrochloric acid under ice-cooling and extracted with ethyl acetate. The extracts were washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.7 g of the desired compound as a colorless oil. NMR spectrum (CDCl3) delta ppm: 1.20-2.45(9.3H,m), 2.65-2.80(0.7H,m), 3.68(3H,s)

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 cyclohexane-1,3-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sankyo Company, Limited; US5843973; (1998); A;,
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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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, A new synthetic method of this compound is introduced below., Recommanded Product: 10601-80-6

General procedure: A mixture of montmorillonite K-10 (75 mg), an appropriate aniline 1 (150 mg, 1.2 mmol), ethyl-3,3-diethoxypropionate (3) (579 mg, 3 mmol) and an aldehyde (166 mg, 1.34 mmol) in pure water (7.5 mL) was stirred at 90 C for the time mentioned in Table 2. After completion of the reaction (indicated by TLC), the mixture was cooled to room temperature and filtered. The filtrate was extracted with EtOAc (3 × 5 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give the desired product.

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Ram; Reddy, G. Rajeshwar; Reddy, L. Srinivasula; Meda, Chandana Lakshmi T.; Parsa, Kishore V.L.; Kumar, K. Shiva; Lingappa; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 395 – 404;,
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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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., name: Ethyl 2,2-difluoroacetate

CuO-ZnO-BaO / CNT catalyst 2 prepared in Example 2 was usedA difluoroethanol was prepared by hydrogenation of difluoroacetate,In a stainless steel autoclave, 35 g of ethyl difluoroacetate and 2 g of catalyst 2 were placed,Closed reactor, the use of 0.5MPa hydrogen replacement kettle air, the introduction of hydrogen pressure of 2MPa,Heating up to 110 C with stirring,Reaction 4 h. Cooling down, until the temperature dropped to 25 after the pressure, open the reactor,After the reaction solution was taken out, the catalyst was separated from the reaction solution, the filtrate was distilled at atmospheric pressure and the pellets were collected at 97 to 99 C,21.5 g of difluoroethanol was obtained, the yield was 93.3%, and the purity was 99%.

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; Shandong Dongyue PolymerMaterial Co., Ltd.; CHEN, YUE; LUO, YONGZHEN; BI, ZUOWEI; (6 pag.)CN105461512; (2016); A;,
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Electric Literature of 1504965-88-1, 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 1504965-88-1 as follows.

The compound (1.83g, 10 mmol) obtained from Preparation Example 83-1 was dissolved in chloroform (50ml), and the solution was cooled to 0. Acetic anhydride (2.36ml, 25mmol) was added thereto, and the solution was stirred for 1 hour at room temperature. Potassium acetate (0.29g, 3mmol) and isopentylnitrite (2.69ml, 20mmol) were added thereto, and the mixture was heated to 70 and stirred for 16 hours. The mixture was cooled to room temperature, diluted with dichloromethane, washed with saturated solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (0.77g, 33%).[1134] NMR:1H-NMR(500HMz, CDCl3); delta 9.00 (d, 1H), 8.14 (s, 1H), 7.46 (d, 1H), 3.98(s, 3H), 2.80 (s, 3H)

According to the analysis of related databases, 1504965-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG LIFE SCIENCES LTD.; LEE, Sung Bae; PAEK, Seung Yup; YOON, Sook Kyung; YOON, Seung Hyun; CHOI, Jeung Soon; WO2014/73904; (2014); A1;,
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Electric Literature of 108928-00-3,Some common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, molecular formula is C9H8F2O2, 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.

B. 2,4-Difluoro-5-nitro-benzoic acid ethyl ester. To 2,4-difluoro-benzoic acid ethyl ester (6.4 g, 34 mmol) at 0 C. was added HNO3/H2SO4 (1:1, 10 mL). The resulting solution was allowed to warm to RT and was stirred for 18 h. The reaction mixture was partitioned between H2O and CH2Cl2 (400 mL). The organic layer was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to provide 7.0 g (88%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7F2NO4, 231.03; m/z not found. 1H NMR (400 MHz, CDCl3): 8.78 (dd, J=8.3, 7.3, 1H), 7.14 (t, J=9.9, 1H), 4.44 (q, J=7.2, 2H), 1.42 (t, J=7.2, 3H).

The synthetic route of 108928-00-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allison, Brett D.; Gomez, Laurent; Grice, Cheryl A.; Hack, Michael D.; Morrow, Brian J.; Motley, S. Timothy; Santillan, Alejandro; Shaw, Karen J.; Schwarz, Kimberly L.; Tang, Liu Y.; Venkatesan, Hariharan; Wiener, John J. M.; US2006/223810; (2006); A1;,
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Reference of 23786-14-3, 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. 23786-14-3, name is Methyl 4-methoxyphenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

Will be 100mLThe two reaction bottles were placed in an ice bath at 0 C.Add 2 g (10.0 mmol) of methyl p-methoxyphenylacetate and 20 mL of acetonitrile.Add p-toluenesulfonyl azide 3a (11.0 mmol),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (15.0 mmol) was slowly added.Stir for 5 minutes in an ice bath and place in a microwave reactor.Set power 400W, heating temperature 40 C, heating time 40 min,Turn on the exhaust fan.After the reaction is completed, the mixture is cooled to room temperature, quenched by the addition of ammonium chloride solution, and extracted with dichloromethane and water. The organic phase is collected, dried over anhydrous sodium sulfate, filtered, and evaporated. Chromatographic separation (eluent is petroleum ether (60-90 C) / ethyl acetate, v / v = 100: 1),The target product 1 g (1.75 g, yield: 85%) was obtained as a red solid.The target product was confirmed by nuclear magnetic resonance spectroscopy and high resolution mass spectrometry.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-methoxyphenylacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nanjing Tech University; Gao Zhen; Yi Xiangyan; Huang Fei; Huang He; Yu Yang; Zhang Zhipeng; Xue Lian; Wang Lize; Qiao Nasen; (12 pag.)CN108727216; (2018); A;,
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