Ethers-buliding-blocks

Electric Literature of 41365-75-7, A common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

N,N-Diisopropylethylamine (3.397 mL, 19.5 mmol) followed by 3,3-diethoxypropan-l- amine (3.154 mL, 19.5 mmol) were added to a solution of 4-chloro-l-fluoro-2- nitrobenzene (1.765 mL, 15 mmol), in iPrOH (35 mL) and heated at 80 C for 4.5 h. After cooling to rt, the reaction mixture was diluted with EtOAc (100 mL) and washed successively with H20 (acidified to ~pH 6 with 0.01 M aqueous HCl, 4chi) and brine (1 x, 100 mL each), dried (MgS04) and the solvent removed under reduced pressure to afford the crude product as an orange solid (4.308 g, 97%). MR (400 MHz, CDC13): delta 8.29 (br s, 1H), 8.17 (d, J= 2.6 Hz, 1H), 7.37 (ddd, J= 9.2, 2.6, 0.6 Hz, 1H), 6.83 (d, J = 9.2 Hz, 1H), 4.65 (t, J= 5.0 Hz, 1H), 3.76-3.65 (m, 2H), 3.59-3.49 (m, 2H), 3.44-3.37 (m, 2H), 2.07-2.01 (m, 2H), 1.24 (t, J= 7.0 Hz, 6H). LRMS (ESI+) m/z 324.9 [M+Na]+ The following intermediate compounds were prepared by the same general procedure.

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; REVIRAL LIMITED; COCKERILL, Stuart George; GOOD, James; (53 pag.)WO2019/16566; (2019); A1;,
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Reference of 6793-92-6, These common heterocyclic compound, 6793-92-6, name is 1-Bromo-4-(phenylmethoxy)benzene, 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.

Nanoporous metal gold catalyst (9.8 mg, 0.05 mmol), ethanol (2 mL) and 4-benzyloxybromobenzene(65.75 mg, 0.25 mmol), cesium carbonate (364.3 mg, 1.125 mmol) was added to the reaction kettle, and hydrogen (40 bar) was added.Heat stirring, the reaction temperature is controlled at 100 C, the reaction time is controlled at 90 h, and the reaction solution is extracted with water to obtain 42.32 mg of biphenyl.The yield was 92%.

Statistics shows that 1-Bromo-4-(phenylmethoxy)benzene is playing an increasingly important role. we look forward to future research findings about 6793-92-6.

Reference:
Patent; Dalian University of Technology; Bao Ming; Zhao Yuhui; Feng Xiujuan; Yu Xiaoqiang; Zhang Sheng; (13 pag.)CN109608297; (2019); A;,
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Application of 113421-98-0,Some common heterocyclic compound, 113421-98-0, name is 4-Fluoro-3-(trifluoromethoxy)aniline, molecular formula is C7H5F4NO, 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.

4-bromo-6-acetylamino-1H-indole-2-carboxylic acid ethyl ester (100 mg, 0.31 mmol), Pd2 (dba) 3 (28 mg, 0.031 mmol), X-phos (30 mg, 0.062 mmol), Cs2CO3 (301 mg, 0.92 mmol) and 3-trifluoromethoxy-4-fluoroaniline (172 mg, 0.92 mmol) were added to a microwave tube, dissolved in 1,4-dioxane (2 mL), and filled with argon Gas-protected, microwave reaction at 100 C for 0.5h, the raw materials disappeared. Cool to room temperature, add EA (20mL), wash with saturated brine (20mL ¡Á 3), wash with water (20mL ¡Á 2), and column chromatography (P / E = 2: 1) to obtain 84mg of a white solid with a yield of 62.2% and a melting point. : 205-206 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-3-(trifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Cui Guonan; Lai Fangfang; Zhou Jie; Ji Ming; Wang Xiaoyu; Du Tingting; Li Ling; Jin Jing; (144 pag.)CN110483366; (2019); A;,
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Reference of 2688-84-8, These common heterocyclic compound, 2688-84-8, name is 2-Phenoxyaniline, 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.

2-Phenoxyaniline (30 mmol) and triethylamine (31.5 mmol) were dissolved in 100 mL of tetrahydrofuran, and the concentration of 2-phenoxyaniline was 0.3 mol/L. The mixture was cooled in an ice-water bath, and stirred. Then oxalyl chloride (15.8 mmol) was added dropwise. The system turned to turbid and triethylamide hydrochloride was formed. The ice-water bath was then removed and the mixture was warmed to room temperature in the air, and continuously stirred for 2 hours until 2-phenoxyaniline was completely consumed (monitored by TLC). Then the stirring was stopped for post process. The stirring bar was removed by a magnetic bar, and tetrahydrofuran was removed by evaporation under reduced pressure. 50 mL of distilled water was added to the resultant residue. The solid on the flask wall was scraped off and immersed into distilled water, and stirred to form slurry. Et3N.HCl was completely dissolved in water while the oxalic diamide was left undissolved. Then the slurry was filtered under reduced pressure, and the solid on filter paper was washed with cold diethyl ether. The residue was removed and dried in an infrared oven, and then dried with an oil pump to afford a white solid (5.45 g, 86% yield). 1H NMR (400 MHz, CDCl3) delta 9.96 (s, 2H), 8.46 (dd, J=8.0, 1.7 Hz, 2H), 7.43-7.30 (m, 4H), 7.22-7.01 (m, 10H), 6.89 (dd, J=8.0, 1.5 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 157.36, 156.06, 146.73, 129.97, 127.97, 125.40, 124.18, 123.75, 120.49, 119.02, 117.60; HRMS (ESI) calcd. for C26H21N2O4 (M+H)+: 425.1496, Found: 425.1492

The synthetic route of 2688-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CE Pharm CO., LTD; Ma, Dawei; Zhou, Wei; Fan, Mengyang; Wu, Haibo; Yin, Junli; Xia, Shanghua; (73 pag.)US10500577; (2019); B2;,
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Electric Literature of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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.

Benzaldehyde (1.58 mL, 15.72 mmol) and 2,2-diethoxyethanamine (3.15 g, 23.58 mmol, 1.5 equiv) were stirred at room temperature for 30 minutes. Triacetoxyborohydride (10 g, 47.18 mmol, 3.0 equiv) was diluted slowly in tetrahydrofuran (150 mL, 10 vol) and slowly added dropwise. The reaction mixture was stirred at room temperature for 12 hours. After the reaction was completed, the mixture was diluted with ethyl acetate (200 mL, 15 vol) and washed once with saturated sodium bicarbonate (200 mL, 15 vol) and water (200 mL, 15 vol). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (n-hexane: ethyl acetate)=1:1 (v/v) to obtain the target compound (3 g, 87%).

The synthetic route of 645-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanmi Pharm Co., Ltd.; Bae In-hwan; Park Chang-hui; Ahn Yeong-gil; (28 pag.)KR2019/40763; (2019); A;,
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Reference of 171290-52-1, 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. 171290-52-1 name is 3,5-Dimethoxyphenylacetylene, 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.

General procedure: trans-1,2-dichloroethylene 7(2.0 equiv.), terminal acetylenes (1.0 mmol, 1.0 equiv.), PdCl2(PPh3)2 (2.0 mol%), CuI (4.0 mol%), piperidine (2.0 equiv.) and 4 mL diethyl ether were mixed together and stirred under nitrogen atmosphere for 6 h. Then the mixture was diluted with water and extracted with dichloromethane. The organic solvent was removed under vacuum and the residue was purified by flash column chromatography (n-hexane : ethyl acetate 10 : 1) to afford the corresponding (E)-chloroenynes 7a-f.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxyphenylacetylene, and friends who are interested can also refer to it.

Reference:
Article; Chuang, Da-Wei; El-Shazly, Mohamed; Chen, Chin-Chau; Chung, Yu-Ming; D. Barve, Balaji; Wu, Ming-Jung; Chang, Fang-Rong; Wu, Yang-Chang; Tetrahedron Letters; vol. 54; 38; (2013); p. 5162 – 5166;,
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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. 32338-02-6, name is 2-Bromo-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 32338-02-6

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

According to the analysis of related databases, 32338-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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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 29578-39-0 as follows. COA of Formula: C7H6BrFO

To a suspension of sodium hydride (60% in mineral oil, 600 mg, 15.0 mmol) inDMF (20 mL) at 65 C was slowly added a solution of 4-hydroxy-l -methylpiperidine (1.15 g, 10 mmol) in DMF (7.0 mL). After stirring for 30 minutes, a solution of 3-bromo-5-fluoroanisole (2.05 g, 10 mmol) in DMF (7.0 mL) was added and the reaction mixture was stirred at 65 C for 24 h. The reaction mixture was allowed to cool to ambient temperature then was poured into water (200 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were loaded onto a SCX-2 cartridge, which was then washed with acetonitrile then eluted with 2N ammonia in methanol. Concentration of the basic methanolic fractions in vacuo gave the title compound (1.5 g, 50%). 1H NMR (CDCl3, 400MHz): 6.65 (dd, J = 2.2, 1.6Hz, 1H), 6.63 (dd, J = 2.3, 1.6Hz, 1H), 6.37 (dd, J = 2.3, 2.1Hz, 1H), 4.29-4.21 (m, 1H), 3.75 (s, 3H), 2.70-2.61 (m, 2H), 2.31-2.21 (m, 5H), 2.01-1.93 (m, 2H), 1.86-1.75 (m, 2H). LCMS (Method B): RT = 2.1 min, M+H+ = 300.

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; WO2009/151598; (2009); 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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H16O4

Example A4 Preparation of the Compound of Formula 70.67 grams of piperidine are condensed with 1,1,3,3-tetramethoxypropane in acetic acid, concentrated and treated with 59.72 grams of 2-ethoxyethyl cyanoacetate cyanoacetate in the presence of an organic base and a solvent. [0228] The following base/solvent combinations are used:The desired product (104) is obtained in yields of 91% (96.5 grams) as an orange powder. [0230] After silica gel column chromatography (eluent: toluene/acetone) the pure product (104) is obtained yielding dark yellow crystals. [0231] Melting point: 66-67 C.

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 102-52-3.

Reference:
Patent; Winkler, Barbara; Hueglin, Dietmar; Eichin, Kai; Ehrsam, Larissa; Marat, Xavier; Richard, Herve; Kienzle, ILona Marion; Schroeder, Ute; US2014/150380; (2014); A1;,
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Synthetic Route of 102-52-3, A common heterocyclic compound, 102-52-3, name is 1,1,3,3-Tetramethoxypropane, molecular formula is C7H16O4, 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 glass-made reactor (inside volume: 2L) equipped with a condenser, thermometer, gas-blowing tube and stirrer was charged with 500 g of 2-methoxy ethanol, into which 36.5 g (1.00 mol) of hydrogen chloride gas was blown at 15C in 1 hour to be dissolved therein, and then 82.0 g (0.50 mol) of malondialdehyde bisdimethylacetal(1,1,3,3-tetramethoxypropane) was added at 10C. Then, 137.0 g (1.10 mols) of 2,3-dimercapto-1-propanol was added immediately to the above mixture at the same temperature, and the resultant mixture was stirred at 25C for 12 hours. After the starting compound was confirmed to disappear by gas chromatography, the reaction mixture was added, with stirring, to 1000 g of water in 30 minutes. The resultant mixture was subjected to extraction with chloroform and washing with water, and separation to obtain an organic phase. Chloroform was distilled at 45C under a vacuum to obtain a singly yellowish, transparent liquid crude product. The crude product thus prepared was purified by silica gel column chromatography (developing solvent: using mixed solvent of toluene/ethyl acetate: 60/40), to obtain 92.4 g (0.325 mol) of the dihydroxy compound represented by the following formula, which was a lightly yellowish crystal, as Example Compound No. (2-a-2). Its yield was 65% on malondialdehyde bisdimethylacetal as the starting compound. ? 270MHz 1H-NMR delta (CDCl3); 2.18 to 2.33 (m, 2H), 3.15 to 3.38 (m, 4H), 3.42 to 3.68 (m, 4H), 3.72 to 3.88 (m, 2H), 4.47 (dq, 2H), 4.72 to 4.78 (m, 2H) ? EI-MS: 284(M)

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsui Chemicals, Inc.; EP1388540; (2004); A1;,
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