Author: Jessica.F

Synthetic Route of 14062-18-1, 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. 14062-18-1, name is Ethyl 2-(4-methoxyphenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 55%NaH(3.29 g, 75.5mmol) was added to dried 1,4-dioxane (20 mL). After vigorously stirring at 30C under N2protection, compound 5 and substituted phenyl ethyl acetates (25.2mmol)were added slowly for 24 hours. After reaction, ethanol was dropped slowly in the mixture until no bubbles are produced. The crude mixture was evaporated invacuo. The residue was stirred vigorously in a biphasic mixture of water (200 mL) andEtOAc(300 mL) at 60C for 0.5 hour. After cooling to room temperature, the organic phase was dried over MgSO4and concentrated invacuo. Finally, the residual solid was recrystallized fromEtOActo afford the target compound6.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-(4-methoxyphenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Huang, Xian-Feng; Cao, Yi-Jing; Zhen, Jing; Zhang, Da-Wei; Kong, Ren; Jiang, Wen-Tao; Xu, Ying; Song, Guo-Qiang; Ke, Heng-Ming; Liu, Li; Bioorganic and Medicinal Chemistry Letters; vol. 29; 3; (2019); p. 481 – 486;,
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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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, A new synthetic method of this compound is introduced below., Safety of Cyclopropanecarboxylic anhydride

Example 9 (diastereomeric mixture)To a solution of example 9a (0.055 g, 0.12 mmol) in dry ACN (2 mL), dicyclopropyl anhydride (0.075 g, 90% content, 0.44 mmol, prepared as described in J. Org. Chem., 67, 5226-5231; 2002) and dry TEA (0.088 mL, 0.62 mmol) are added and the mixture heated under microwaves irradation (100C) for 50 min and then heated at 150C for additional 30 min. Solvents evaporated, crude purified by flash cromatography (cycloheane/EtOAc from 50:50 to 20:80) to obtain the title compound (0.033 g, 54%).HPLC-MS (Method 6): Rt = 10.80 minMS (ESI pos): m/z = 486 (M+H)+ The diastereoisomers of the title compound are separated by HPLC using a chiral stationary phase.Method for separation:HPLC apparatus type: Agilent 1100; column: Daicel chiralpack AS-H, 5.0 muiotaeta, 250 mm x 20 mm; method: eluent hexane/EtOH 70:30; flow rate: 15 mL/min, Temperature: 25C; UV Detection: 230 nm Example of separation by chiral HPLC:Sumitted to separation: 200 mg of Example 9Obtained: 84 mg of Diastereoisomer 1 (Exp. 10) and 78 mg of Diastereoisomer 2 (Exp.11)Example Chiral HPLC HPLC-MS (Method 5): MS (APCI pos):Rt [min] Rt [min] m/z

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; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; WO2013/17657; (2013); A1;,
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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. 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 6933-47-7

Step (viii): Methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate. A suspension of 217 3-chloro-4-ethoxy 5-isopropoxybenzoic acid (48: R2=iPr, R3=Et) (2.82g, 10.9mmol) and 145 methyl 4-amino-2-methylbenzoate (38: R1=Me) (2.16g, 13.1mmol) in 45 ethyl acetate (33mL) was treated with 46 triethylamine (4.56mL, 32.7mmol) followed by 44 T3P (50wt% in ethyl acetate) (17.34mL, 27.3mmol) and the mixture was heated at 60C for 4h and allowed to cool to room temperature for 16h. The reaction mixture was stirred vigorously with an aqueous solution of 218 sodium hydrogencarbonate (50mL) for 10min and separated. The aqueous layer was extracted with dichloromethane (3×100mL) and the combined organic phases were dried (magnesium sulfate), filtered concentrated in vacuo and the residue purified by silica gel chromatography (40g, 0:50:50 to 20:40:40 ethyl acetate:120 dichloromethane:isohexane) to produce 219 methyl 4-(3-chloro-4-ethoxy-5-isopropoxybenzamido)-2-methylbenzoate as a beige solid (3.24g, 70% yield). 1H NMR (400MHz, CDCl3) delta 8.0 (1H, d, J=8.4Hz), 7.8 (1H, s), 7.59-7.50 (2H, m), 7.43-7.36 (2H, m), 4.69-4.73 (1H, m), 4.18 (2H, q, J=7.1Hz), 3.92 (3H, s), 2.6 (3H, s), 1.46-1.37 (9H, m). m/z 406 [M+H]+ (ES+), 404 [M-H]- (ES-).

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:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 73792-08-2, COA of Formula: C8H8FNO2

A suspension of 5,6,7,7a,8,9,10, 11-octahydro-4H-2-benzo[ef]heptalenecarboxylic acid (0.090 g) in anhydrous benzene (3 ml) was added with thionyl chloride (1 ml), and the mixture was refluxed by heating for 3 hours. The reaction mixture was concentrated under reduced pressure, the resulting residue was dissolved in anhydrous benzene (2 ml) and pyridine (5 ml), the solution was added with methyl 2-fluoro-4-aminobenzoate (0.075 g) and 4-dimethylaminopyridine (one pellet), and the mixture was stirred overnight. The reaction mixture was added with 2 N aqueous hydrochloric acid and thereby made acidic, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 10% aqueous sodium carbonate, and saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane = 1:10) to obtain methyl 2-fluoro-4-[(5,6,7,7a,8,9,10,11-octahydro-4H-2-benzo[ef]heptaleny)carboxamido]benzoate (0.052 g, yield: 36%). 1H-NMR (400MHz, CDCl3): delta 1.51-1.71 (6H, m), 1.79-1.95 (6H, m), 2.91 (4H, t, J=5.7 Hz), 3.26-3.32 (1H, m), 3.92 (3H, s), 7.31 (1H, dd, J=8.4, 2.1 Hz), 7.41 (2H, s), 7.77 (1H, dd, J=12.9, 2.1 Hz), 7.94 (1H, br-s), 7.95 (1H, t, J=8.4 Hz)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Research Foundation Itsuu Laboratory; EP2189443; (2010); A1;,
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Related Products of 37746-78-4, 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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4-hydroxy-3,5-dimethylbenzaldehyde(13a)(1.5 g, 10 mmol) and ethyl4-bromobutanoate (1.95g, 10mmol) were dissolved in acetonitrile (100 mL) andtreated with K2CO3 (5.52g, 40mmol). The reaction mixturewas stirred at 80 C for 24 h.Water was added to thereaction,and the aqueouslayer was extracted with EA (3 × 20 mL). The organic layers were combined,washed with water (3 × 25 mL),dried over anhydrous Na2SO4,and concentrated in vacuo to give compound 14aa(1.87g,71%).

The chemical industry reduces the impact on the environment during synthesis (E)-Ethyl 4-bromobut-2-enoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Shao, Mingfeng; He, Linhong; Zheng, Li; Huang, Lingxiao; Zhou, Yuanyuan; Wang, Taijing; Chen, Yong; Shen, Mingsheng; Wang, Fang; Yang, Zhuang; Chen, Lijuan; Bioorganic and Medicinal Chemistry Letters; vol. 27; 17; (2017); p. 4051 – 4055;,
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Synthetic Route of 18927-05-4, 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. 18927-05-4, name is Methyl 3-Methoxyphenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of sodium hydride (13.2 g, 303.6 mmol) in dimethylformamide (350 mL) was added methyl 3-methoxyphenylacetate (25 g, 138 mmol) and methyl acrylate (31 ml, 345 mmol) in dimethylformamide (160 mL) at 0C, then the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated in vacuo. The residue was purified by silica gel chromatography to give 42.8 g of the title compound as a colorless oil. High-performance liquid chromatography/mass spectrometry m/z 321(M+H) Retention time: 3.61 min.

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, Methyl 3-Methoxyphenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
Ester – Wikipedia,
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Application of 15963-40-3, The chemical industry reduces the impact on the environment during synthesis 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of Et2Zn (11.89 mL, 11.89 mmol) in DCM (10 mL) was added a solution of TFA (0.88 mL, 11.89 mmol) in DCM (10 mL) dropwise at 0 C for 30 minutes. A solution of CH2I2 (0.96 mL, 11.89 mmol) in DCM (10 mL) was added dropwise at 0 C for 45 minutes. The reaction mixture was stirred at 0 C for 1 hour. A solution of methyl 3- methylenecyclobutanecarboxylate (500 mg, 3.96 mmol) in DCM (5 mL) was added to the reaction mixture. The reaction mixture was allowed to warm to 15 C for 16 hours. Saturated NH4CI solution (50 mL) was added to the reaction mixture and the mixture was extracted with DCM (50 mL c 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by silica gel column chromatography (10 % EtOAc in petroleum ether) to afford the title compound (400 mg, 72 %) as a yellow oil. ‘ H NMR (400 MHz, CDCl3) d 3.71 (s, 3H), 3.34 – 3.27 (m, 1H), 2.53 – 2.48 (m, 2H), 2.26 – 2.20 (m, 2H), 0.49 – 0.42 (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, Methyl 3-methylenecyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
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Reference of 27007-53-0, These common heterocyclic compound, 27007-53-0, name is Methyl 2-bromo-5-chlorobenzoate, 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.

Step 2. methyl 5-chloro-2-cyanobenzoate To a stirred solution of methyl 2-bromo-5-chlorobenzoate (11.5 g, 46 mmol) in degassed DMF (50 mL) was added zinc cyanide (2.82 g, 24.0 mmol) and palladium tetrakis-triphenylphosphine (1.0 g, 0.86 mmol) and the mixture was heated to 90 C. for 18 h. The reaction was partitioned between EtOAc (200 mL) and water (100 mL). The organic phase was concentrated in vacuo and the residue was purified by flash chromatography eluding with a gradient of 10%, 15%, 20% ethyl acetate in hexane yielding methyl 5-chloro-2-cyanobenzoate as a white solid (8.0 g, 88% yield). TLC Rf=0.4 (15% EtOAc-hexanes); HPLC RT=3.13 min (Method A); 1H NMR (CDCl3, 400 MHz) 8.13 ppm (d, 1H, J=1.83 Hz); 8.09 ppm (d, 1H, J=8.24 Hz); 7.29 ppm (dd, 1H, J=8.34, 2.10 Hz); 4.02 ppm (s, 3H). Step. 3 2-aminomethyl-5-chlorobenzyl Alcohol

The synthetic route of 27007-53-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Williams, Peter D.; Lyle, Terry A.; Morrissette, Matthew M.; Tran, Lekhanh O.; Staas, Donnette D.; US2003/13700; (2003); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 541-16-2, A common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, molecular formula is C11H20O4, 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: A mixture of 2-(3, 4-dichlorophenyl)acetonitrile (5 mmol), ditert-butyl malonate (3 mmol), and Fe(ClO4)3·H2O (5 mol%) wasplaced in a round-bottomed flask. Then, the reaction mixturewas heated at 80 C for 5 h. After completion of the reactionmonitored by thin layer chromatography (TLC), water (10 mL)was added and the reaction mixture was extracted with ethylacetate (3 × 20 mL). The organic layers were collected, combined,washed with water (3 × 20 ml), dried over anhydrousNa2SO4, and concentrated under vacuum. The pure product wasobtained by directly passing through a silica gel (200-300mesh) column to give a white powder 1m (1.08 g, 84% yield).Compound 1m1H NMR (400 MHz, CDCl3): delta = 7.41-7.35 (m, 2 H), 7.12-7.10 (m,1 H), 5.31 (s, 1 H), 3.40 (s, 2 H), 1.32 (s, 9 H) ppm. 13C NMR (100MHz, CDCl3): delta = 168.9, 135.6, 132.7, 131.2, 131.2, 130.6, 128.6,51.6, 43.5, 28.7 ppm. HRMS: m/z calcd for C12H15Cl2NO [M + H]+:259.0531; found: 259.0533.

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:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
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Related Products of 1195768-18-3, 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. 1195768-18-3 name is Methyl 3-amino-2-fluorobenzoate, 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 an ice-cold solution of (2S,4R)-l-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2- carboxylic acid (1.24 g) in DCM (25 mL), was added l-chloro-N,N,2-trimethylprop-l-en-l- amine (0.845 mL, 1.2 equiv) dropwise with stirring. The stirring was continued for 3 hours at this temperature. Methyl 3-amino-2-fluorobenzoate (0.9 g) was then added followed by DIEA (2.78 mL, 3 equiv). The cooling bath was removed and the reaction mixture was stirred overnight at rt. The solvent was co-evaporated with MeOH (3 mL). The remaining residue was then dissolved in chloroform (30 mL) and washed successively with cold 1 N aq HC1 (3 x 20 mL), water (30 mL), and a saturated aq NaHCCb solution (30 mL). The organic layer was dried (Na2S04) and concentrated under reduced pressure to afford the title compound as an amber oil. Used without purification for the next step.

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

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
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