Category: 133803-81-3

Electric Literature of 133803-81-3 ,Some common heterocyclic compound, 133803-81-3, molecular formula is C11H22O5, 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.

To a solution of tert- butyl 3-[2-(2-hydroxyethoxy)ethoxy]propanoate (350 mg, 1.49 mmol) in DCM (15 ml) was added TEA (0.62 ml, 4.48 mmol), then the reaction mixture was cooled to 0 C (water ice/acetone bath) and Mesyl chloride (0.14 ml, 1.79 mmol) was added dropwise. The reaction mixture was stirred for 1 h at room temperature. By TLC no starting material (Hex:AcOEt, 3:7). Reaction mixture was poured into an aqueous solution of NaHC03 (20 mL) and product extracted with DCM (20mL, 2x), the organic extracts were combined, dried (Na2S04), and evaporated under vacuum. The crude product (mesylate) was used in the next step without any further purification (>95% pure by NMR): 1H NMR (500 MHz, Chloroform-d) delta 4.44 – 4.28 (m, 2H), 3.76 (dd, J = 5.2, 3.8 Hz, 2H), 3.70 (t, J = 6.4 Hz, 2H), 3.68 – 3.57 (m, 4H), 3.07 (s, 3H), 2.49 (t, J = 6.4 Hz, 2H), 1.45 (s, 9H). [00400] Crude mixture from previous step was diluted in Acetonitrile (5 ml) and Nal (335.88 mg, 2.24 mmol) was added, the reaction mixture was stirred at 70 C for 12 h (overnight). By TLC no starting material (Hex:AcOEt, 7:3), the reaction was poured into an aqueous solution of Na2S203 (10%, 50 mL) and product was extracted with DCM (2×50 mL). Organic extracts were combined, dried (Na2S04) and evaporated under vacuum. Crude product was purified by flash chromatography (SiO2-40g, grad. Hex:AcOEt, 2 to 40% in 15 min), to give 413 mg of product as an oil (80% yield). 1H NMR (500 MHz, Chloroform-d) delta 3.73 (dt, J = 13.5, 6.6 Hz, 4H), 3.68 – 3.54 (m, 4H), 3.24 (t, J = 6.9 Hz, 2H), 2.50 (t, J = 6.5 Hz, 2H), 1.44 (s, 9H). 13C NMR (151 MHz, cdcl3) delta 171.00, 80.69, 72.11, 70.50, 70.27, 67.09, 36.39, 28.25, 3.02. LC- MS ESI); m/z: [M+Na]+ Calcd. for CnH2iI04Na, 367.0382. Found 367.0943.

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. 133803-81-3, tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARVINAS, INC.; YALE UNIVERSITY; CREW, Andrew P.; DONG, Hanqing; WANG, Jing; CREWS, Craig M.; JAIME-FIGUEROA, Saul; (496 pag.)WO2018/226542; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 133803-81-3, 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. 133803-81-3, name is tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate, molecular formula is C11H22O5, The 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.

DIAD (730 muL, 3.60 mmol) was added dropwise to a stirred solution of 3-methoxy-5-nitrophenol (510 mg, 2.99 mmol), tert-butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate (700 mg, 2.99 mmol) and triphenylphosphine (950 mg, 3.59 mmol) in THF (4 mL) at 0-5 C. The reaction was allowed to warm to rt and stirred at this temperature overnight. The reaction mixture was concentrated in vacuo. The crude product was purified by chromatography on silica gel (80 g column, 0-100% EtOAc in isohexane) to afford the sub-title compound (1.13 g) as a yellow oil, which solidified on standing. The product was used in the next without further purification. 1H NMR (400 MHz, DMSO-d6) delta: 7.34-7.32 (m, 2H), 6.98 (t, 1H), 4.21-4.19 (m, 2H), 3.85 (s, 3H), 3.76-3.74 (m, 2H), 3.60-3.56 (m, 4H), 3.52-3.50 (m, 2H), 2.40 (t, 2H), 1.38 (s, 9H).

According to the analysis of related databases, 133803-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Topivert Pharma Limited; Respivert Limited; BAKER, Thomas Matthew; FYFE, Matthew Colin Thor; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; MEGHANI, Premji; RIGBY, Aaron; SAMBROOK-SMITH, Colin; THOM, Stephen Malcolm; US2014/296208; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 133803-81-3, Adding some certain compound to certain chemical reactions, such as: 133803-81-3, name is tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate,molecular formula is C11H22O5, 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 133803-81-3.

ferf-Butyl 3 (2 (2- hydroxyethoxy)ethoxy)propanoate (8.6 g, 37 mmol) was added to a suspension of Dess- Martin periodinane (DMP, 18.8 g, 44 mmol) and pyridine (7.0 g, 88 mmol) in DCM (150 mL) at 0C. The resulting mixture was stirred at room temperature for 16 hours, then filtered, washed with DCM (3 x 50 mL). The filtrate and washings were combined and washed with saturated NaHC03 solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane:EtOAc = 10: 1 to 3: 1) to give the title compound (4.1 g, 48%) as a yellow oil. 1H NMR (400 MHz, CDC13): delta 9.76 (s, 1H), 4.16 (s, 2H), 3.50-3.80 (m, 6H), 2.53(t, 2H), 1.46 (s, 9H).

According to the analysis of related databases, 133803-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 133803-81-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 133803-81-3, name is tert-Butyl 3-(2-(2-hydroxyethoxy)ethoxy)propanoate. This compound has unique chemical properties. The synthetic route is as follows.

At 0 C,To tert-butyl 3- (2- (2-hydroxyethoxy) ethoxy) propionate (6.24 g, 26.63 mmol, 1.0 eq.) And TsCl (10.15 g, 53.27 mmol, 2.0 eq.) In anhydrous To a solution of dichloromethane (50 mL) was added pyridine (4.3 mL, 53.27 mmol, 2.0 eq.).The mixture was stirred at room temperature overnight,Then washed with water (100 mL),The aqueous layer was extracted with dichloromethane (3 ¡Á 50 mL).The combined organic layers were washed with brine (300 mL),Dried over anhydrous sodium sulfate, filtered,Concentrated and purified by silica gel column chromatography (5: 1 n-hexane / ethyl acetate),A colorless oil was obtained (6.33 g, 61.3% yield).

According to the analysis of related databases, 133803-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangzhou Duo Xi Biological Technology Co., Ltd.; Zhao Luoboyongxin; Huang Yuanyuan; Yang Qingliang; Gai Shun; Ye Hangbo; Xu Yifang; Guo Huihui; Cao Minjun; Li Wenjun; Cai Xiang; Zhou Xiaomai; Xie Hongsheng; Jia Junxiang; Guo Zhixiang; Lin Chen; Yang Yanlei; Ye Zhicang; Qi Tafamingrenqingqiubugongkaixingming; (338 pag.)CN110621673; (2019); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts