Tag: M.W=100-200

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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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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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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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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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, 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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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. 144267-96-9, name is Ethyl 3,4-difluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 3,4-difluorobenzoate

The ester required for the preparation of Example 19b was prepared as follows: Ethyl 3-fluoro-4-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[(1H-pyrazol-3- ylamino)carbonyl]phenoxy}benzoate; To a suspension of tert-butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1- methylethoxy] benzoyl} amino)-lH-pyrazole-l-carboxylate (587 mg, 1.5 nunol), caesium carbonate (488 mg, 1.5 mmol) in DMA (3 mL) was added ethyl 3,4-difluorobenzoate (279 mg, 1.5 mmol). This mixture was heated at 110C for 16 hours. The reaction mixture was filtered and concentrated in vacuo then the residue chromatographed on silica, eluting with 0- 70% ethyl acetate in hexane, to give the desired compound as a yellow oil (271 mg, 40%) tu NMR (CDC13) : 1.3 (d, 3H), 1.4 (t, 3H), 3.4 (s, 3H), 3.5 (m, 2H), 4.4 (q, 2H), 4.6 (m, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.1 (s, 1H), 7.15 (s, 1H), 7.3 (s, 1H), 7.5 (d, 1H), 7.8 (d, 1H), 7.85 (d, 1H), 9.4 (s, 1H)

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/80359; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6627-89-0, name is tert-Butyl phenyl carbonate, 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 6627-89-0, SDS of cas: 6627-89-0

Preparation of 1-(-N-Boc-aminomethyl)-4-(aminomethyl)benzene [0178] [0179] Tert-butylphenyl carbonate (2.7 mL, 14.7 mmol) was added dropwise to a solution of p-xylylenediamine (2 g, 14.7 mmol) in ethanol (20 mL) at 80 C. The reaction mixture was refluxed overnight. The solution was then cooled to room temperature and any solids were removed, which leaves a yellow solution. The solution was then concentrated to 10 mL and diluted with water (60 mL). The solution pH was adjusted to 3 with 2M HCl followed by an extraction with dichloromethane (3×75 mL). The water solution pH was then adjusted to pH 12 followed by extraction with dichloromethane (3×75 mL). The organic solutions were combined and washed with sodium bicarbonate (2×75 mL), dried with sodium sulfate, and concentrated down to a white solid. Characterization matches previously published literature (M. A. Ghanem, et al., ?Covalent modification of glassy carbon surface with organic redox probes through diamine linkers using electrochemical and solid-phase synthesis methodologies?, Journal of Materials Chemistry, (2008), 18(41), pg 4917-4927).

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, tert-Butyl phenyl carbonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; INTERNATIONAL BUSINESS MACHINES CORPORATION; Coady, Daniel Joseph; Engler, Amanda Catherine; Fukushima, Kazuki; Hedrick, James Lupton; Liu, Shaoqiong; Maune, Hareem Tariq; Nelson, Alshakim; Pitera, Jed Walter; Yang, Yi Yan; US2013/281515; (2013); A1;,
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Application of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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: Methyl 4-amino-3-methylbenzoate (6) (10.00g, 60.58mmol) was acylated with alkyl acyl chloride (90.87mmol) and triethylamine (16.79mL, 121.16mmol) in DCM at 0C. The resulting amide was reacted with fuming nitric acid in sulfuric acid (60%) at-20C. The resulting nitro-compound was reduced with hydrogen (5bar) and Raney Ni (0.79g, 13.34mmol) in methanol at 100C. The resulting amino compound was dissolved in glacial acetic acid and heated under reflux for 1h. After evaporation of the acetic acid, water was added and the pH was adjusted to 9 by addition of concentrated ammonia. This solution was extracted with ethyl acetate (3×100mL). The combined organic layers were washed with aqueous NaHCO3 solution and dried over MgSO4. After filtration, the solvent was removed under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-methylbenzoate, its application will become more common.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
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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. 14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C10H11ClO2

EXAMPLE 19 6-(3-Chlorobenzyl)-1-(2-trifluoromethylphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 157 mg (70% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.56 mmol) of 5-amino-1-(2-trifluoromethylphenyl)-1H-pyrazole-4-carboxamide (Example 27A), 0.339 g (1.67 mmol) of ethyl (3-chlorophenyl)acetate and 0.111 g (2.78 mmol) of 60% sodium hydride. m.p.: 152 C. MS (ESI pos): m/z=405 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.9 (s, 2H), 7.15-7.5 (m, 4H), 7.6-8.05 (m, 4H), 8.3 (s, 1H), 12.5 (s, 1H) ppm.

The synthetic route of 14062-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer HealthCare AG; US2007/161662; (2007); A1;,
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