Category: esters-buliding-blocks

Electric Literature of 46064-79-3,Some common heterocyclic compound, 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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 methyl 2-oxocyclooctanecarboxylate (32.0 g, 174 mmol), methyl 3-amino-4-bromobenzoate (20.0 g, 87 mmol) and ethanol (120 mL) was heated to reflux, at an oil bath of 130 C., acetic acid (1.5 mL) was added and the mixture was reflux for 1.5 hours. Hot PPA (200 g, 120 C.) was added to the reaction mixture carefully. The reaction mixture was heated at an oil bath of 130 C. for 3 hours. After cooling for a while, ice (200 g), ethyl acetate (60 mL) and petroleum ether (60 mL) were added to the reaction mixture, the mixture was concentrated until 200 mL solvent was removed. Then water (600 mL) and ethyl acetate (60 mL) were added, the resulting mixture was stayed at room temperature overnight. A light brown solid was slowly formed. The mixture was filtered and the filtered cake was dried to give a light brown solid, which was placed into methanol (90 mL). SOCl2 (30 mL) was added dropwise with cooling with an ice-bath. The resulting mixture was heated to reflux for 4 hours, concentrated and treated with saturated NaHCO3 solution (60 mL) and ethyl acetate (30 mL), filtered and the filtered cake was dried to give desired product (6.6 g) as a pale white solid (21%).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhou, Changyou; Ren, Bo; Wang, Hexiang; US2015/18356; (2015); A1;,
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Application of 756525-95-8, These common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, 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 compound 301 (8.16 g, 35.0 mmol, 1.0 eq. ) and saturated NaHCO3(40 mL) was cooled to 0 , to which compound 409 (5.43 g, 35.0 mmol, 1.0 eq. ) was added in portions. After stirring at 0 for 1 h, the reaction was warmed to r.t. and stirred for 1 h. The reaction was extracted with DCM (3 × 100 mL) and the organic extract was washed with brine, dried over anhydrous Na2SO4, concentrated and purified by SiO2column chromatography to give a white solid (6.76 g, 62%yield) . MS ESI m/z calcd for C15H23NO6[M+H]+314.15, found 314.15.

Statistics shows that tert-Butyl 9-Amino-4,7-dioxanonanoate is playing an increasingly important role. we look forward to future research findings about 756525-95-8.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); 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. 117324-05-7, name is Ethyl 2-amino-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H10FNO2

Step B: To the formamide (6 mL) solution of ethyl-2-amino-4-fluorobenzoate (811 mg, 4.43 mmol) added ammonium formate (0.450 g, 7.14 mmol) and the reaction mixture was heated at 140 C. overnight. After cooling added water and ethyl acetate. The layers were separated, the EtOAc layer was dried, filtered and evaporated to give desired quinazolinone (1 g, quantitative). MS (ES) 165 (M+H)

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 117324-05-7.

Reference:
Patent; Pandey, Anjali; Scarborough, Robert M.; Matsuno, Kenji; Ichimura, Michio; Nomoto, Yuji; Ide, Shinichi; Tsukuda, Eiji; Sasaki, Junko; Oda, Shoji; US2004/186110; (2004); 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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 3-(dimethylamino)acrylate

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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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 116419-94-4 as follows. category: esters-buliding-blocks

Method 23; 4-Bromomethyl-3-trifluoromethyl-benzoic acid methyl esterA suspension of 4-methyl-3-trifluoromethyl-benzoic acid methyl ester (Method 22;0.327 g, 1.5 mmol), iV-bromosuccinimide (267 mg, 1.5 mmol) and benzoyl peroxide (0.15 mmol) in CCl4 (10 ml) was heated to reflux for 3 h. The reaction mixture was cooled to25 C, filtered through a pad of silica gel, and washed with DCM. The organics were removed under reduced pressure and the crude product was purified by column chromatography utilizing an ISCO system (hexanes/EtOAc) to give 252 mg (56.5%). NMR: 7.70-8.25 (m,3H), 4.85 (s, 2H)5 3.91 (s, 3H); m/z 297.

According to the analysis of related databases, 116419-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/79791; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 15963-40-3, These common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, 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.

3.1.57b (24 g, 190.4 mmol, 1.0 equiv) was dissolved in THE and cooled to -15 C. BH3.Me2S (14.4 g, 190.4 mmol, 1.0 equiv) was added drop wise and the reaction mixture was stirred at room temperature for 4 hours. Cooled the reaction mixture at -15 C, NaOH (3M) (25 mL), H202 (50%) (12.9 g, 190.4 mmol, 1.0 equiv) were added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sodium bisulphate and extracted with EtOAc. The organic layer was washed with brine,dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (70 % EtOAc in Hexane) to afford product 3.1.57c (18.7 g, 68 % yield). 1H NMR (400 MHz, DMSO) 64.54 (d, J = 29.8 Hz, 1H), 3.62-3.55 (m, 3H), 3.41 (d, J = 6.5 Hz, 1H), 3.30 (d, J = 6.0 Hz, 1H), 3.13-2.95 (m, 1H), 2.37-2.27 (m, 1H), 2.15 (ddt, J= 8.7, 7.8, 6.2 Hz, 2H), 1.98- 1.84(m, 2H).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
Ester – Wikipedia,
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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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, A new synthetic method of this compound is introduced below., name: Diethyl 1,1-cyclopropanedicarboxylate

Synthesis of 1-(ethoxycarbonyl)cyclopropanecarboxylic acid Diethyl 1, 1-cyclopropane dicarboxylate (20g) was hydrolyzed in IN NaOH (107 m4) and ethanol (220D) for 16 hours, and the ethanol was removed by distillation under reduced pressure. The remaining starting material was removed by using ethyl acetate and the aqueous layer was acidified by IN HCI. The reaction mixture was extracted with ethyl acetate and distilled under reduced pressure. The residue was purified by silica gel column to give the title compound in a yield of 94%. 1H NMR(CDCl3) No. 1.06 (t, 3H), 1.53 (m, 2H), 1.62 (m, 2H), 4.21 (q, 2H) ESI: 159 +1) +C7H1004

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; ANADYS PHARMACEUTICALS, INC.; WO2005/79812; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3196-15-4, name is Methyl 2-bromobutyrate, A new synthetic method of this compound is introduced below., HPLC of Formula: C5H9BrO2

Sodium sulfite (12.61 g, 0.1 mol) and sodium bicarbonate (8.40 g, 0.105 mol) were added to 100 mL of water and 10 mL of tetrahydrofuran and then stirred. When the salts dissolved completely, IX (18.05 g, 0.05 mol) was added and the temperature of 15 C was maintained for 12 h, while stirring. Upon the reaction completion, the precipitated solid was obtained by filtration and the filter cake was directly added to a stirred mixture of 2-bromobutyric acid methyl ester (9.05 g, 0.05 mol) and methanol (200 mL), which was then heated to 60 C. The progress of the reaction was monitored by GC up to complete disappearance of 2-bromobutyric acid methyl ester. The resulting mixture was then cooled to room temperature and the first precipitated solid was removed by filtration. VI was further crystallized from the filtrate. Yield: 18.27 g (85.6 %). Melting point: 47.9-48.9 C.

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Yun-Long; Wang, Ling; Qian, Chao; Tao, Ming; Liao, Zu-Tai; Chen, Xin-Zhi; Chemical Papers; vol. 69; 9; (2015); p. 1237 – 1243;,
Ester – Wikipedia,
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Electric Literature of 14064-10-9,Some common heterocyclic compound, 14064-10-9, name is Diethyl 2-chloromalonate, molecular formula is C7H11ClO4, 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 1: diethyl 2-(3-chloro-5-cyanophenoxy)malonate To a solution of 3-chloro-5-hydroxybenzonitrile (14 g, 72 mmol) in acetone (150 mL) was added potassium carbonate (18 g, 130 mmol) and diethyl 2-chloromalonate (10 g, 65 mmol). The mixture was heated at 80° C. for 2 hr. After cooling to r.t., the mixture was concentrated under reduced pressure to remove most of acetone, diluted with water, extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give diethyl 2-(3-chloro-5-cyanophenoxy)malonate (20 g) which was used without further purification.

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

Reference:
Patent; Arrington, Kenneth L.; Burgey, Christopher; Gilfillan, Robert; Han, Yongxin; Patel, Mehul; Li, Chun Sing; Li, Yaozong; Luo, Yunfu; Lei, Zhiyu; US2014/100231; (2014); A1;,
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Application of 77820-58-7, 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 77820-58-7 as follows.

Example 81 – Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloro-anthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for 5 hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15% sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67% yield, mp 56-68C. IR and 1H NMR spectra were in agreement with the assigned structure.

According to the analysis of related databases, 77820-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics