Month: May 2021

Reference of 1462-12-0, These common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, 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 8 3,6-Dimethyl-5-oxoheptanoic acid 8-A. (1,4-Dimethyl-3-oxopentyl)propanedioic acid, diethyl ester A cold (0 C.) solution of 2,2,6,6-tetramethylpiperdine (10.241 gm, 72.5 mmol) in tetrahydrofuran (120 mL) was treated with n-butyl lithium (2.5 M in hexane, 29.0 mL, 72.5 mmol). The light yellow solution was stirred at 0 C. for 30. minutes, then cooled to -78 C. and treated with neat methyl isopropyl ketone (7.70 mL, 6.20 gm, 72 mmol) over a five-minute period. After 50 minutes, a solution of diethyl ethylidenemalonate (10.000 gm, 53.7 mmol) in tetrahydrofuran (7 mL) was added to the above mixture over a 10-minute period. After 50 minutes, the mixture was quenched with glacial acetic acid (5.0 ml) and warmed to room temperature. The mixture was poured into 50% saturated ammonium chloride and extracted with ethyl ether. The ethyl ether extract was washed with 1 N hydrochloric acid, water, and brine, then dried (magnesium sulfate), filtered and stripped to give a pale yellow oil. Distillation of the oil (P=0.15-0.2 mm Hg) afforded compound 8-A (10.883 gm, 74%) as a colorless liquid which boiled at 110-114 C. Thin layer chromatography: Rf =0.25 (20% ethyl acetate in hexane).

The synthetic route of 1462-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5072023; (1991); A;,
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Adding a certain compound to certain chemical reactions, such as: 213598-10-8, name is Methyl 3-bromo-4-isopropoxybenzoate, 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 213598-10-8, Recommanded Product: Methyl 3-bromo-4-isopropoxybenzoate

Compound 22-1 (200 mg, 0.732 mmol) was dissolved in MeOH (5.00 mL). Lithium hydroxide monohydrate (61.5 mg, 1.46 mmol) and water (1.00 mL) were added. The mixture was stirred at 10 C. for 16 hours. The reaction solution was concentrated. The residue was added in water (3 mL) and extracted with dichloromethane (5 mL×1). The organic phase was discarded. The aqueous phase was adjusted to pH 5-6 with hydrochloric acid (1 mol/L), and extracted with dichloromethane (5 mL×2). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to afford compound 22-2.1H NMR: (400 MHz, CDCl3) delta 8.31 (d, J=2.0 Hz, 1H), 8.02 (dd, J=2.0, 8.8 Hz, 1H), 6.94 (d, J=8.8 Hz, 1H), 4.81-4.61 (m, 1H), 1.44 (d, J=6.0 Hz, 6H).

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-bromo-4-isopropoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDSHINE DISCOVERY INC.; ZHANG, Peng; WU, Lingyun; YIN, Jun; LI, Jian; CHEN, Shuhui; (121 pag.)US2020/48235; (2020); A1;,
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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. 2521-91-7, name is Ethyl 2-((3-bromophenyl)amino)acetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H12BrNO2

General procedure: A mixture of sodium methoxide (10 mmol) and hydroxylaminehydrochloride (6 mmol) in anhydrous methanolwaswell stirred for30 min. To this mixture was added compound 5 or 6 (3 mmol) wasadded, and the mixture was stirred at room temperature for 1-3 h.The reaction was quenched with ice (30 g) and neutralized withdilute HCl, which was extracted with ethyl acetate (3 60 mL). Theorganic layers were collected, dried over sodium sulfate, filtered,and evaporated under vacuum. The residure was purified by flashsilica chromatography (methanol-dichloromethane) to afford pureproduct (2 or 3) as a white solid.

According to the analysis of related databases, 2521-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Qi; Shi, Wei-Kang; Ren, Shen-Zhen; Ni, Wei-Wei; Li, Wei-Yi; Chen, Hui-Min; Liu, Pei; Yuan, Jing; He, Xiao-Su; Liu, Jia-Jia; Cao, Peng; Yang, Pu-Zhen; Xiao, Zhu-Ping; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 126 – 136;,
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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 577-62-8 as follows. Recommanded Product: 577-62-8

A solution of compound 2 (3mmol) in 10 mL ethanol and refluxed with 99 % hydrazine hydrate (6 mmol) for 4 h and the reaction was monitored by using TLC after completion. The reaction mass was cooled to room temperature and then poured into 50 mL cold water. The precipitate was filtered off.

According to the analysis of related databases, 577-62-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Navudu, Ramesh; Mannem, Gangadhara Rao; Bollikolla, Hari Babu; Asian Journal of Chemistry; vol. 28; 6; (2016); p. 1351 – 1360;,
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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. 93-92-5, name is 1-Phenylethyl acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Phenylethyl acetate

General procedure: A 1,2-dichloroethane (5.0mL) solution of isopropenyl acetate (2a) (0.3mmol), 1-phenylethyl acetate (10a) (0.3mmol) and ReBr(CO)5 was stirred under an atmosphere of nitrogen at 80C for 5h. After the reaction was complete, H2O was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with MgSO4. The resulting mixture was filtered, and the filtrate was concentrated. Purification of the residue by silica gel column chromatography afforded 4-phenyl-2-pentanone (3a). The product (3a) was characterized by comparing its spectral data with those of authentic sample [23].

The synthetic route of 93-92-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Umeda, Rui; Takahashi, Yuuki; Yamamoto, Takaaki; Iseki, Hideki; Osaka, Issey; Nishiyama, Yutaka; Journal of Organometallic Chemistry; vol. 877; (2018); p. 92 – 101;,
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Electric Literature of 153597-59-2,Some common heterocyclic compound, 153597-59-2, name is Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate, molecular formula is C9H12N2O3, 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.

N-Bromosuccinimide (6.00 g, 33.7 mmol) was added portion-wise to a solution of C2 (6.00 g, 30.6 mmol) in acetonitrile (100 mL). After the reaction mixture had been stirred at 50 C for 1 hour, it was allowed to cool to room temperature, concentrated in vacuo, and partitioned between ethyl acetate (200 mL) and water (150 mL). The organic layer was washed with water (150 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 20% to 80% ethyl acetate in heptane) provided material that contained residual succinimide; this was dissolved in ethyl acetate (100 mL), washed with water (2 x 100 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting yellow solid was triturated with pentane to afford the product as a white powder. Yield: 6.00 g, 21.8 mmol, 71 %. LCMS m/z 276.9 (0287) (bromine isotope pattern observed) [M+H]+. 1H NMR (400 MHz, CDCI3) delta 4.44-4.40 (m, 2H), 4.42 (q, J=7.1 Hz, 2H), 4.26 (t, J=6.2 Hz, 2H), 2.36-2.29 (m, 2H), 1 .41 (t, J=7.1 Hz, 3H).

The synthetic route of 153597-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; PATEL, Nandini Chaturbhai; VERHOEST, Patrick Robert; HELAL, Christopher John; SCIABOLA, Simone; LACHAPELLE, Erik Alphie; WAGER, Travis T.; HAYWARD, Matthew Merrill; (127 pag.)WO2017/145013; (2017); A1;,
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Related Products of 238749-50-3,Some common heterocyclic compound, 238749-50-3, name is Ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, molecular formula is C9H8BrNO2S, 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.

Ethyl 2-bromo-6-formyl-4H-thieno[3,2-b]pyrrole-5-carboxylate (62). To DMF(2.05 mL) cooled by ice/water was added POCl3 dropwise and the mixture was stirred for 30 min. A solution of carboxylate 61 (1.96 g, 7.15 mmol) in DMF (2.5 mL) was added at this temperature and the mixture was allowed to warm to room temperature then heated to 60 0C. After 16 h, the reaction mixture was cooled to room temperature, and poured into ice/water. The mixture was extracted with EtOAc (3×20 mL) and the combined organic layers were washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4. After removed the organic solvent, the residue was purified by column chromatography (EtOAc/Hexane: 1/4) to give the desired aldehyde 62 (1.62 g, 75%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-bromo-4H-thieno[3,2-b]pyrrole-5-carboxylate, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; THOMAS, Craig J.; AULD, Douglas S.; INGLESE, James; SKOUMBOURDIS, Amanda P.; JIANG, Jian-Kang; BOXER, Matthew; WO2010/42867; (2010); A2;,
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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. 1260092-46-3, name is tert-Butyl 3-(2-aminoethoxy)propanoate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 3-(2-aminoethoxy)propanoate

To a solution of fert-butyl 3-(2-aminoethoxy)propanoate (246 mg, 1.302 mmol) in DMF (1.5 ml) at rt was added bis(2,5-dioxopyrrolidin-l-yl) 3,3′-oxydipropanoate (232 mg, 0.651 mmol) and followed DIPEA (0.284 ml, 1.628 mmol). The mixture was allowed to stir at rt over night and concentrated to dryness. To the resulting residure at 0 C was added 1.0 mL neat TFA, and the resulting mixture was allowed to stir at rt overnight. The mixture was concentrated to give the crude product, which was used without further purification. UPLC-MS Method A: TR = 0.7 min, m/z = 393 (z = 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; MERCK SHARP & DOHME CORP.; LIN, Songnian; YAN, Lin; HUO, Pei; PISSARNITSKI, Dmitri; FENG, Danqing; NARGUND, Ravi; MADSEN-DUGGAN, Christina; ZHU, Yuping; KEKEC, Ahmet; WU, Zhicai; (191 pag.)WO2017/205309; (2017); A1;,
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Electric Literature of 210530-71-5, 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. 210530-71-5, name is Methyl 2-(3,4-difluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows.

2-(3,4-Difluorophenyl)acetylhydrazide (B4)(analogously to WO2004/101512A2, Bioorg. Med. Chem. Lett. 2004, 14(3), 817-822)1.0 g of methyl 2-(3,4-difluorophenyl)acetate (C4) is dissolved in 6.0 ml of 2-propanol. 365 mul of hydrazinium hydroxide are subsequently added, and the reaction solution is heated under reflux for 18 h overnight. The mixture is then evaporated to dryness in vacuo and purified by flash column chromatography on silica gel (solvent gradient: ethyl acetate/0-10% by vol. of ethanol), giving 803 mg of the title compound as a colourless solid having a melting point of 112 C.; MS: 187.1 (MH+); TLC: Rf=0.50 (ethyl acetate/ethanol 9:1 parts by volume).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-(3,4-difluorophenyl)acetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG; US2011/224302; (2011); A1;,
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13031-39-5, name is 3-Chlorophenyl acetate, 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. Application In Synthesis of 3-Chlorophenyl acetate

4-Chloro-2-hydroxyacetophenone.; 3-Chlorophenyl acetate (10 g, 0.0588 mol) was heated together with aluminum chloride (13.86 g, 0.105 mol) at 160 C for 2 hours. The mixture was poured on water and extracted with diethylether. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was dissolved in methanol. The solution was treated with charcoal, filtered and water was added to the filtrate. The resulting oil was extracted with diethylether. The organic layer was dried over magnesium sulfate and diethylether was evaporated under reduced pressure. The resulting oil was used without further purification (77 %). IR (KBr) : u : 3436 (O-H), 3073 (C-H aromatic), 1643 (C=O) cni 1.

The synthetic route of 13031-39-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LIEGE; UNIVERSITE LIBRE DE BRUXELLES; WO2005/75463; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics