Esters-buliding-blocks

25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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.

A mixture of 4.203 g (25 mmol) of ethyl 4,4,4-trifluorocrotonate, 20 mL of nitromethane and ca. 0.576 g (5 mmol) of tetramethyl guanidine was stirred for 13 hours at room temperature, and then diluted with water and acidified by the addition of 0.5 M sulfuric acid. The mixture was extracted three times with diethyl ether. The combined ether extracts were washed with water, and then brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5.601 g (98%) of 4,4,4-trifluoro-3-nitromethyl-butyric acid ethyl ester as an amber oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 25597-16-4.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Zhi; ERICKSON, Shawn David; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/60341; (2014); A1;,
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4224-69-5,Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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.

To a stirred mixture of methyl 2-(bromomethyl)acrylate (239 mul, 2 mmol) in petroleum ether (3 ml) was added potassium carbonate (276 mg, 2 mmol), followed by sodium methoxide (119 mg, 2.2 mmol) and methanol (450 mul). The resulting mixture was stirred overnight, filtered, concentrated to a residue that was purified by column chromatography eluting with 10% ether in hexanes to provide the title compound (150 mg, 58%). (Reference: J. Med.Chem.; 42; 15; 1999; 2760-2773.)

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

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, molecular formula is C5H7BrO2, 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. 4224-69-5

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4224-69-5, its application will become more common.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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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 46064-79-3 as follows. 46064-79-3

Triethylamine (61 mg, 0.60 mmol) was added to a mixture of crude 2-methoxy-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid (110 mg, 0.5 mmol) (from Example 18 supra) and HATU (0.23 g, 0.6 mmol) (Aldrich) in DMF (5.0 mL) at room temperature. The resulting mixture was stirred until clear solution was obtained (light brown). Methyl 3-amino-4-bromobenzoate (0.14 g, 0.6 mmol) (Oakwood) was added. The mixture was stirred for another 20 hours. Precipitate formed. Water (50 mL), aqueous saturated sodium bicarbonate solution (10 mL), and ethyl acetate (30 mL) were added. After thorough mixing, pale yellow precipitate was collected by filtration, washed with water and ethyl acetate and dried in vacuum oven. Residue was recrystallized from DMF-ethyl acetate-hexanes to give product as pale yellow crystals. (Yield 0.04 g, 18.5%).HR-MS (ES+) m/z Calculated for C17H14BrN4O5 ([M+H]+): 433.0142. Found: 433.0143.

According to the analysis of related databases, 46064-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
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2005-10-9, The chemical industry reduces the impact on the environment during synthesis 2005-10-9, name is 6H-Benzo[c]chromen-6-one, I believe this compound will play a more active role in future production and life.

2a (58.8 mg, 0.3 mmol), NaBH4 (17.1 mg, 0.45 mmol) and EtOH (3 mL) was added to a flask (10 mL) and stired for 6 h at room temperature. The reaction mixture was wished with CH2Cl2 (3 x5 mL) and filtered through Celite. After evaporation of the solvent under vacuum, the residue was purified by column chromatography on silica gel (100-200 mesh) using petroleum ether-EtOAc (10/1, V/V) as eluent to give pure 6. 4.4.1. 6H-benzo[c]chromen (6)Prepared from 6H-benzo[c]chromen-6-one; isolated as whitesolid (50.3 mg, 92%), m.p. 130-132 C; 1H NMR (500 MHz, CDCl3):d 7.52-7.50 (m, 1H), 7.42-7.40 (m, 2H), 7.29-7.26 (m, 2H), 7.12 (dd,J1 7.5 Hz, J2 1.5 Hz, 1H), 7.02-6.99 (m, 1H), 6.95 (d, J 8.5 Hz,1H), 4.48e4.42 (m, 2H); 13C NMR (125 MHz, CDCl3): d 152.9, 138.9,136.5,130.9,130.8,129.4,129.3,128.6,128.5,127.8,120.8,116.4, 63.7.

The chemical industry reduces the impact on the environment during synthesis 6H-Benzo[c]chromen-6-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui; Tetrahedron; vol. 73; 2; (2017); p. 154 – 163;,
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25597-16-4, A common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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.

The resulting product (0.45g, 1.9mmol) from step 4, ethyl 4,4,4-trifluorocrotonate (1.3g, 7.6mmol) and anhydrous potassium carbonate (2.6g, 1.9mmol) were dissolved in DMF (10mL), and then the system was stirred for 2hrs at 90C. 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 0.40g 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+)

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Institute 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; EP2845854; (2015); A1;,
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These common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

General procedure: To an undivided electrochemical cell, fitted with an iron/nickel (64/36) rod as the anode and surroundedby a nickel foam as the cathode, were added DMF (50 mL), tetrabutylammonium bromide (1.2 mmol, 400mg), and 1,2-dibromoethane (2.5 mmol, 215 muL). The mixture was electrolyzed under argon at a constantcurrent intensity of 0.2 A at room temperature for 15 min. The current was then stopped, and the NiBr2bpycomplex (0.4 mmol, 150 mg), 3-amino- or 3-alkoxy/aryloxy-6-chloropyridazine (4 mmol), and aromatic orheteroaromatic halides (8 mmol) were sequentially added. The solution was electrolyzed at 0.2 A at roomtemperature until one of the starting materials was totally consumed. A saturated aqueous solution of EDTAsodium salt (100 mL) was added to the mixture, and the solution was extracted with dichloromethanecontaining 2-5% methanol (3 ¡Á 100 mL). The combined organic layers were dried over MgSO4, filtered,and evaporated under vacuum. The crude product was purified by flash chromatography on silica, elutedwith a gradient of solvents (pentane/acetone). For some polar cross-coupling compounds, a mixture ofacetone/methanol (95/5) was necessary.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 24398-88-7.

Reference:
Article; Sengmany, Stephane; Sitter, Mathilde; Leonel, Eric; Le Gall, Erwan; Loirand, Gervaise; Martens, Thierry; Dubreuil, Didier; Dilasser, Florian; Rousselle, Morgane; Sauzeau, Vincent; Lebreton, Jacques; Pipelier, Muriel; Le Guevel, Remy; Bioorganic and Medicinal Chemistry Letters; vol. 29; 5; (2019); p. 755 – 760;,
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Ester – an overview | ScienceDirect Topics

24398-88-7, A common heterocyclic compound, 24398-88-7, name is Ethyl 3-bromobenzoate, molecular formula is C9H9BrO2, 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.

1-(6-(dibutyl(3-(ethoxycarbonyl)phenyl)stannyl)hexyl)-3-ethyl-1H-imidazol-3-ium bromide I’a-14(Br-) A dried 50 mL Schlenk tube was flushed with argon and charged with zinc dust (1.36 g, 20.8 mmol, 5 eq) and cobalt(II) bromide (0.095 g, 0.4190.434 mmol, 0.1 eq). The mixture was activated under vacuum at 150C during 4 h. Acetonitrile (5 mL) was added to the cooled mixture then trifluoroacetic acid (0.15 mL) and 1,2-dibromoethane (0.1 mL) were added and the resulting solution stirred for additional 15 minutes (an increase of temperature was observed). Then ethyl 3-bromobenzoate (1.46 g, 6.36 mmol, 6.3 eq) was introduced to the mixture which was stirred at room temperature for 12 h. The resulting solution of arylzinc reagent was introduced dropwise to the ionic liquid (Va-1) (529 mg, 1.0 mmol, 1 eq) in solution in THF (6 mL). After 18 h of stirring at room temperature, the resulting mixture was filtered through a short pad of silica gel then extracted with CH2Cl2 (3 x 100 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (CH2Cl2 to CH2Cl2/MeOH 90:10) to afford compound I’a-14(Br-) as viscous yellow oil (450 mg, 70 %). 1H NMR (CDCl3): delta 10.17 (s, 1H), 8.14 (bs, 1H), 7.92 (d, J = 7.8 Hz, 1H), 7.62 (d, J = 7.2 Hz, 1H), 7.39 (dd, J = 7.5 Hz, J = 7.5 Hz, 1H), 7.30 (bs, 1H), 7.23 (bs, 1H), 4.48-4.33 (m, 4H), 4.32 (t, 2H, J = 7.2 Hz), 1.89-1.78 (m, 2H), 1.61-1.47 (m, 9H), 1.42-1.24 (m, 11H), 1.13-1.00 (m, 6H), 0.87 (t, J = 7.2 Hz, 6H). 13C NMR 75 MHz (CDCl3) delta (ppm): 166.8, 141.9, 140.6, 136.9, 135.9, 129.4, 128.8, 127.5, 122.0, 121.8, 60.6, 49.8, 45.1, 33.4, 30.0, 28.7, 27.0, 26.3, 25.5, 15.5, 14.4, 13.4, 9.4, 9.3. HRMS (FAB) calcd. for C28H47N2O2Sn 563.2654 [M-Br]+; found 563.2675.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Centre National de la Recherche Scientifique (CNRS); UNIVERSITE DE NANTES; UNIVERSITE D’ANGERS; Universite du Maine; Institut National de la Sante et de la Recherche Medicale (INSERM); Centre Hospitalier Universitaire De Nantes; Legoupy, Stephanie; Faye, Djibril; Gestin, Jean-Francois; Rajerison, Holisoa; Faivre-Chauvet, Alain; Boeda, Fabien; EP2891657; (2015); A1;,
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Ester – an overview | ScienceDirect Topics

25597-16-4, A common compound: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step 6: ethyl 8-chloro-6-(methyl-D3)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (0.25 g, 1.4 mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (0.48 g, 2.8 mmol) and anhydrous potassium carbonate (0.46 g, 2.8 mmol) were dissolved in DMF (10 mL), and then the system was stirred for 3 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 0.2 g of the product (44%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta 7.39 (s, 1H), 7.31 (s, 1H), 6.1 (m, 1H), 4.27 (dd, 2H), 1.30 (t, 3H) MS (MM-ES+APCI), m/z: 325 (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

Some common heterocyclic compound, 1865-29-8, name is Methyl 2-phenylacrylate, molecular formula is C10H10O2, 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. 1865-29-8

PREPARATION 21 Methyl (RS)-4-cyano-2-Phenylbutanoate STR75 Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78 C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil. 1 H-NMR (300 MHz, CDCl3), delta=2.0-2.4 (m, 4H), 3.7 (s, 3H), 3.8 (t, 1H), 7.2-7.5 (m, 5H) ppm. I.R. (thin film) 2220 cm-1 (C=N).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1865-29-8, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5292749; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics