Month: January 2021

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. 27798-60-3, name is Methyl 2-Methoxyphenylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H12O3

General procedure: A solution of 2.5 M n-BuLi in hexane (1.2 equiv) was added dropwise to a solution of HMDS (1.2 equiv) in anhyd THF at -78 C under argon, and then, after stirring of the mixture for 10 min, a solution of alkyl 2-arylacetate (1 equiv) in THF was added in one portion. The mixture was stirred for 10 min, after which a solution of acyl chloride (1.15 equiv) in THF was added in one portion and the mixture was stirred for 15 min at -78 C and then overnight at r.t. The reaction mixture was quenched with sat. aq NH4Cl, extracted with EtOAc or Et2O, and the organic layer was washed with brine and dried over Na2SO4. The solvents were evaporated to give 3-substituted alkyl 2-aryl-3-oxopropanoate 5, which was used without further purification. NH2OH¡¤HCl (2-5 equiv) was added to a solution of 5 in MeOH and the mixture was refluxed for 24 h. The solvent was evaporated, the residue was treated with H2O, and the precipitate that formed was filtered, washed with H2O and a mixture of PE/EtOAc (10:1), and then dried in air to give pure 3-substituted 4-aryl-5-hydroxyisoxazole/4-arylisoxazol-5(4H)-one 6. The yields of 6 were calculated for the two steps, and is based on the starting alkyl 2-arylacetate.

The synthetic route of 27798-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bodunov, Vladimir A.; Galenko, Ekaterina E.; Galenko, Alexey V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Synthesis; vol. 50; 14; (2018); p. 2784 – 2798;,
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Application of 25597-16-4, The chemical industry reduces the impact on the environment during synthesis 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, I believe this compound will play a more active role in future production and life.

Step 5: ethyl 6-bromo-5,7-(dimethyl-D6)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (0.45 g, 1.9 mmol) from step 4, ethyl 4,4,4-trifluorocrotonate (1.3 g, 7.6 mmol) and anhydrous potassium carbonate (2.6 g, 1.9 mmol) were dissolved in DMF (10 mL), and then the system was stirred for 2 hrs at 90 C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.40 g of the product (55%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.88 (s, 1H), 6.76 (s, 1H), 5.7 (m, 1H), 4.3 (dd, 2H), 1.35 (t, 3H) MS (MM-ES+APCI), m/z: 384 (M-H+)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 6065-82-3, name is Ethyl diethoxyacetate, 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. Quality Control of Ethyl diethoxyacetate

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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Reference of 66315-16-0, A common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, molecular formula is C9H12N2O2, 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.

Intermediate 44: 2-(2,6-Difluoro-phenylamino)-l -methyl- lH-benzoimidazole-5-carboxylic acid 44.1 : 2-(2,6-Difluoro-phenylamin -l-methyl-lH-benzoimidazole-5-carboxylic acid ethyl ester A mixture of 2.00 g (10.3 mmol) 3-amino-4-methylamino-benzoic acid methyl ester and 1.76 g (10.3 mmol) 2,6-difluorophenyl isothiocyanate in 50 mL acetonitrile and 10 mL DMF was stirred at RT for 12 h. 1.80 g (14.3 mmol) Nu,Nu’-diisopropylcarbodiimide was added and the mixture was stirred at 80 C for 5 h. The solvent was removed by distillation. The residue was taken up in EtOAc. The precipitate was filtered off and washed with EtOAc and diethyl ether. The residue was taken up in acetonitrile. The precipitate was filtered off, washed with acetonitrile and diethyl ether and dried. yield: 2.20 g (64 %) ESI-MS: m/z = 332 (M+H)+ Ri(TLC): 0.30 (DCM/MeOH = 19: 1)

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

105-76-0, name is Dibutyl maleate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Dibutyl maleate

Example 3 N-(3-Triethoxysilylpropyl)-aspartic acid di-n-butyl ester 221.0 g (1.0 mol) of 3-aminopropyl-triethoxysilane and 228.0 g (1.0 mol) of maleic acid di-n-butyl ester were reacted by the same procedure used in Example 1. The viscosity of the clear, pale yellow liquid was about 30 mPa.s (23 C). Base titration showed an amine equivalent weight of about 462 g (theory: 449 g).

The synthetic route of 105-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US5364955; (1994); A;,
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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Computed Properties of C4H7ClO3

Example 3K (R)-3-{N-(5′-Chloro-2′-fluorobiphenyl-4-ylmethyl)-N’-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic Acid Ethoxycarbonyloxymethyl Ester 2,6-Lutidine (407 mg, 3.8 mmol) was added to a solution of (R)-3-{N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)-N’-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic acid (200 mg, 380 mmol), carbonic acid chloromethyl ester ethyl ester (105 mg, 760 mumol) and NaI (114 mg, 760 mumol) in DMF (10 mL). The mixture was stirred overnight at room temperature. Water (30 mL) was added and the mixture was extracted with EtOAc (3*40 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (MeCN-H2O (0.1% TFA); Gradient 60-70) to yield the title compound as a white solid (56 mg). LC-MS: 630.1 [M+H]+. 1H-NMR: (CD3OD-d4, 400 MHz) delta 1.24 (t, J=5.9 Hz, 3H), 3.30-3.33 (m, 2H), 4.17-4.32 (m, 4H), 4.45 (t, J=4.2 Hz, 1H), 5.78 (br, 2H), 7.20-7.28 (m, 1H), 7.57-7.29 (m, 10H), 7.92-7.95 (m, 1H).

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hughes, Adam D.; Fleury, Melissa; US2013/330365; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate, molecular formula is C8H6BrFO2, 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. HPLC of Formula: C8H6BrFO2

To methyl 3-bromo-4-fluorobenzoate (3.02 g, 13.0 mmol) in ether (30 ml) at 0 C. add dropwise MeMgBr (3.0M in ether, 11 ml, 33 mmol). Stir 1 h and pour onto ice. Acidify with 1N HCl, separate the ether, wash with 1N NaHCO3, dry (MgSO4), and concentrate to obtain the product as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 82702-31-6, its application will become more common.

Reference:
Patent; Schering Corporation; US2005/239795; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 39149-80-9, name is tert-Butyl 2-bromopropanoate, 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 39149-80-9, Product Details of 39149-80-9

Sodium hydride (60% dispersion in mineral oil) (1.02 g, 25.43 mmol) was added to a solution of methyl 2-(2-bromo-4-fluorophenyl)acetate (5.24 g, 21.19 mmol) and 1,3- dimethyl-3,4,5,6-tetrahyaYo-2(lH)-pyrimidinone (2.56 mL, 21.19 mmol) in anhydrous THF (50 mL). The reaction mixture was stirred for 15 min. before a solution of tert-butyl- 2-bromopropionate (5.32 g, 25.43 mmol) in anhydrous THF (5 mL) was added to it. The reaction mixture was stirred at room temperature overnight. The reaction mixture was heated to 60C for a further 24 h. After that time, the mixture was cooled to room temperature and poured onto water. The mixture was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo. The crude material was purified by column chromatography on silica, eluted with 10% EtOAc/hexane to afford the title compound. (0689) ?H NMR (400 MHz, CDCb) 8ppm 0.87 – 1.01 (m, 2 H), 1.19 (s, 4 H), 1.23 – 1.29 (m, 1 H), 1.46 (s, 5 H), 2.92 – 3.23 (m, 1 H), 3.55 – 3.72 (m, 3 H), 4.29 – 4.46 (m, 1 H), 6.94 – 7.07 (m, 1 H), 7.26 – 7.49 (m, 2 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 2-bromopropanoate, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LIWICKI, Gemma; MACK, Stephen; STEPHENSON, Anne; TEALL, Martin; WHITE, Kathryn; (168 pag.)WO2018/47983; (2018); 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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., Recommanded Product: Diethyl fluoromalonate

General procedure: All flasks and stirrer bars were flame dried before use. To the N-oxide (0.2 mmol, 1.0 equiv.), dissolved in 2 cm3 dichloromethane was added Tf2O (0.3 mmol, 1.5 equiv.) at 0 C. In another flask, a suspension of NaH (0.7 mmol, 3.5equiv.) in 1 cm3 tetrahydrofuran was cooled to 0 C and the malonate (0.7 mmol, 3.5 equiv.) was added. After 15 min, the malonate solution was added to the activated N-oxide solution and the mixture was stirred at room temperature for 1 h. The reaction was quenched with NH4Cl solution and the aqueous phase was extracted with dichloromethane. The combined organic layers were washed with brine before being dried over MgSO4. The solvents were removed under reduced pressure and the crude product was purified by column chromatography.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lemmerer, Miran; Teskey, Christopher J.; Kaiser, Daniel; Maulide, Nuno; Monatshefte fur Chemie; vol. 149; 4; (2018); p. 715 – 719;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4841-22-9, name is Methyl 2-(4-chlorophenoxy)acetate, molecular formula is C9H9ClO3, 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. Application In Synthesis of Methyl 2-(4-chlorophenoxy)acetate

To the obtained methyl 4-chlorophenoxyacetate, 401.74 g of 25% sulfuric acid was added, and the acid hydrolysis reaction was carried out at 80 C for 2 h.At the same time, the alcohol formed by the reaction is distilled off, and the reaction is cooled to room temperature and filtered.The filter cake was washed with a small amount of water, and the filter cake was dried to obtain 182.27 g of 4-chlorophenoxyacetic acid.The content was 98.6%, and the total yield was 96.31% based on phenol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4841-22-9, its application will become more common.

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Chi Zhilong; Zhang Liguo; Hu Yishan; (13 pag.)CN108947839; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics