Month: May 2021

These common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, 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. name: Ethyl 2-butynoate

General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3·H2O (2 × 5 mL), distilled water (5 mL), and acetone (2 × 5 mL) and reused in the next run. The filtrate was washed with water (2 × 10 mL) and brine (2 × 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.

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

Reference:
Article; Hu, Wenli; Yang, Weisen; Yan, Tao; Cai, Mingzhong; Synthetic Communications; vol. 49; 6; (2019); p. 799 – 813;,
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Application of 14062-24-9, 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 14062-24-9 as follows.

Ethyl trifluoroacetate (3.57 g, 25.2 mmol) and sodium (580 mg, 25.2 mmol) were added to a solution of ethyl 2-(4-chlorophenyl)acetate (5.0 g, 25.2 mmol) in ether (8 mL), followed by heating to reflux for 24 hours. After the reaction was completed, 2N hydrochloric acid (50 mL) was added thereto, and the resultant product was extracted with ether (20 mL*3). The mixed organic layer was washed with water (20 mL*3), and dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), whereby ethyl 2-(4-chlorophenyl)-4,4,4-trifluoro-3-oxobutanoate (2.42 g, yield: 34%) was obtained as a yellow solid.

According to the analysis of related databases, 14062-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
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These common heterocyclic compound, 2065-23-8, name is Methyl 2-phenoxyacetate, 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. SDS of cas: 2065-23-8

To the methyl phenoxyacetate obtained by distillation,0.09 g of 99% pure lead acetate and 1.29 g of 99% pure 2,3,4-trichlorothiophene were added.118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react.After the addition, the reaction was kept at this temperature for 0.5 h.The fraction was distilled at a pressure of 1 kPa and collected at 110 to 120 C to obtain 200.87 g of methyl 4-chlorophenoxyacetate, and the content was 98.84%.

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

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Chi Zhilong; Zhang Liguo; Hu Yishan; (13 pag.)CN108947839; (2018); A;,
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Electric Literature of 104670-74-8, The chemical industry reduces the impact on the environment during synthesis 104670-74-8, name is Methyl 2-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

Example 83: Synthesis of 2-amino-3-[2-(3- hydroxyphenyl)ethynyl]benzoic acid 2-amino-3-[2-(3-hydroxyphenyl)ethynyl]benzoic acid: To a sealed tube was loaded a mixture of 2-amino-3-bromo-benzoic acid methyl ester (50 mg, 0.22 mmol), Pd(PPh3)2Cl2 (15.4 mg, 0.022 mmol) and Cul (4.2 mg, 0.022 mmol) in triethyl amine (1 mL). The mixture was degassed with N2 for 10 minutes, 3- ethynyl-phenol (103 mg, 0.87 mmol) was added and the mixture degassed with N2 for 5 minutes. The reaction mixture was heated at 90 C for 5 hours. After cooling to ambient temperature, the crude mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated and purified by preparative thin layer chromatography eluting with ethyl acetate/hexane (30%) to give a solid intermediate. To the solid intermediate in tetrahydrofuran/methanol (1 mL/0.2 mL) was added sodium hydroxide solution (2 N in water, 0.2 mL, 0.4 mmol) and the solution was stirred at room temperature for 18 hours. 1 N hydrochloric acid aqueous solution was added dropwise until pH = 1 and the reaction mixture was purified through preparative HPLC to give 11 mg (14% for 2 steps) of the pure product as a white solid. LCMS (ESI) mlz 254.1 (M+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, Methyl 2-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE WISAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy, E.; SMITH, Garry, R.; REITZ, Allen, B.; LIEBERMAN, Paul, M.; WO2015/73864; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35065-86-2, name is 3-Bromophenyl acetate, 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 35065-86-2, Safety of 3-Bromophenyl acetate

In a 250 mL round bottom flask (8) (5.49 g, 26 mmol) and anhydrous AlCl3 (6.92 g, 51 mmol) was mixed thoroughly on oil bath at 160 C for 2 h. Reaction mixture was poured into ice water and concentrated hydrochloric acid solution was added to break complex formed during reaction. The mixture was taken in AcOEt (50 mL * 3). The organic layer was combined and washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 30:1) gave (9) (3.85 g, 70 %) as white solid. Mp: 36-38 C, MS (EI) [M]+: m/z = 213, 1H NMR (400 MHz, CDCl3) delta ppm: 7.60 (d, J = 8.0 Hz, 1H), 7.20 (s, 1H), 7.07 (d, J = 8.0 Hz, 1H), 2.63 (s, 3H).

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

Reference:
Article; Wang, Chen; Gao, Hongping; Dong, Jinyun; Zhang, Yanmin; Su, Ping; Shi, Yaling; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 277 – 284;,
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Some common heterocyclic compound, 51122-91-9, name is Dimethyl Isopropylmalonate, molecular formula is C8H14O4, 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: C8H14O4

EXAMPLE 1; 382 g (406 ml) of DMF were initially charged in a Schmizzo and 137 g (141 ml) of 1.0 eq. NaOMe (30% solution in methanol) were added. This mixture was then heated to 60 C. (+/-3 C.) and 131 g (0.753 mol) of dimethyl isopropylmalonate were metered in within one hour. Subsequently, a methanol/DMF mixture (201 g) was distilled off under pressure (300 mbar to 60 mbar) and a temperature of 60 C.Thereafter, at 80 C. (+/-3 C.), 86 g (79 ml, 0.779 mol, 1.03 eq.) of 1,3-dichloropropene were metered in within one hour and the reaction mixture was then heated at 80 C. (+/-3 C.) for two hours. The reaction mixture was heated to 140 C. and a 25% solution of LiCl (0.6 eq.) in methanol (19 g of LiCl in 58 g of methanol) was metered in within two hours, and the reaction mixture was heated at 140-142 C. for a further 6 hours, in the course of which a portion of the methanol was distilled off and approx. 1.5 mol of gas (mainly CH3Cl and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters. On completion of reaction, the solvent (DMF) and the excess methanol were distilled off substantially fully under reduced pressure. The remainder was admixed with 200 g of water, 89 g of 34% HCl and 200 g of MTBE, and the phases were separated. The organic phase was washed lx with 50 g of water and the solvent was removed under reduced pressure. Approx. 140 g of product were obtained, of which approx. 125 g were ester and 13 g the corresponding acid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51122-91-9, its application will become more common.

Reference:
Patent; DSM Fine Chemicals Austria NFG GMBH & Co KG; US2008/207943; (2008); A1;,
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Synthetic Route of 35120-18-4,Some common heterocyclic compound, 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, molecular formula is C7H11BrO2, 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 solution of (5Z,8Z,1 1 Z,14Z,17Z)-icosa-5,8,1 1 ,14,17-pentaene-1 -thiol (305 mg, 1 .00 mmol) in dry DMF (10 mL) at 0C under inert atmosphere was added NaH (60% in mineral oil, 44 mg, 1 .1 mmol). After fifteen minutes ethyl 2-bromo-cyclobutane carboxylate (170 muIota_, 1 .05 mmol) was added and the mixture was stirred for 1 .5 hour at 0C. The reaction was quenched by addition of sat. aq. NH4CI (20 mL). Heptane (50 mL) was added, and the phases were separated. The water phase was extracted with heptane (2×25 mL). The combined organics were washed with water (25 mL) and brine (25 mL), dried (MgSC ), filtered and evaporated to give 409 mg of the title compound as a crude oil. Purification by flash chromatography on silica gel using isocratic elution (heptane:acetone 98:2) afforded 243 mg (56% yield) of the title compound as oil. 1 H- NMR (300 MHz, CDCI3): delta 0.95 (t, 3H), 1.27 (t, 3H), 1 .42 (d, 3H), 1.54 (m, 2H), 1.84 (m, 1 H), 1 .96-2.23 (m, 7H), 2.51 (m, 2H), 2.60 (m, 2H), 2.73-2.90 (m, 8H), 4.18 (m, 2H), 5.23-5.43 (m, 10H); MS (CI (CH4)): 471 [M+C3H5]+, 459 [M+C2H5]+, 431 [M+H]+, 385 [M-OEt]+, 357 [M-C02Et]+, 303 [R-S],+.

The synthetic route of 35120-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRONOVA BIOPHARMA NORGE AS; STEINEGER, Hilde; (38 pag.)WO2016/173923; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 606-45-1, name is Methyl 2-methoxybenzoate, 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 606-45-1, Product Details of 606-45-1

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C.

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 2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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Synthetic Route of 37722-82-0, The chemical industry reduces the impact on the environment during synthesis 37722-82-0, name is Methyl 3-Hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

Methyl 1-oxaspiror2.5loctane-5-carboxylateTo a solution of trimethylsulfoxonium iodide (53.3 g, 242 mmol) in dry DMSO (300 ml.) under N2, was added sodium hydride (9.69 g, 242 mmol) portionwise over 30 min. This light yellow mixture was stirred at RT for 1 h. The reaction mixture was then cooled in an ice bath and treated with methyl 3-oxocyclohexanecarboxylate (29.0 g, 186 mmol) dropwise while maintaining a temperature at or below 27 C. The resulting reaction mixture was allowed to warm slowly to RT and stir overnight. The reaction was diluted with water and extracted with DCM. The combined organics were washed with water, dried over MgS04, filtered, and concentrated to provide methyl 1-oxaspiro[2.5]octane-5-carboxylate (31.8 g, 85 % yield) which was used without further purification. H NMR (400 MHz, CDCI3) delta 3.66 (s, 3H), 2.71 (m, 1 H), 2.65 (d, J = 1.76 Hz, 2H), 2.00 (dd J = 1 1.8, 13.6 Hz, 2H), 1.74 – 1.85 (m, 2H), 1.60 – 1.74 (m, 1 H), 1.40 – 1.56 (m, 2H), 1.17 – 1.32 (m, 1 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, Methyl 3-Hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; HOANG, Tram, H.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2013/12500; (2013); 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. 206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H10BrNO2

Example 134 5-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester To a stirred solution of 24.5 g (100 mmol) of the product of Example 133 in 100mL of pyridine was added 21.0 g (100mmol) of p-methoxybenzenesulfonyl chloride and the resulting mixture was heated to 80 C for 24 h. The reaction mixture was then quenched with ice cold water and acidified with concentrated HCl. The resulting mixture was extracted with chloroform, washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with diethyl ether, filtered and dried to provide 35g (84%) of the desired product as a brown solid. Electrospray Mass Spec 416, (M+H).

According to the analysis of related databases, 206548-14-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
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