With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.14320-38-8, name is Cyclopent-3-enol, molecular formula is C5H8O, molecular weight is 84.12, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks
To an ice-cooled solution of 4-hydroxycyclopentene (50.0 g, 0.594 mol) and imidazole (80.9 g, 1.19 mol) in N,N-dimethylformamide (300 mL) was slowly added tert-butyldiphenylsilyl chloride (180 g, 0.65 mmol). The reaction mixture was warmed toroom temperature. After 16 h, the reaction mixture was diluted with water (1 L) and ethyl acetate (500 mL). The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The combined organics were washed sequentially with water (3 x 300 mL) and saturated aqueous sodium chloride solution (2 x 200 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography(15:1 petroleum ether / ethyl acetate) providedtert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (188 g, 98 %) as a colorless oil. 1H NMR (400 MHz, CDC13): oe: 7.69 – 7.66 (m, 4H), 7.43 – 7.38 (m, 6H), 5.63 – 5.60 (m, 2H), 4.58 – 4.53 (m, 1H), 2.46 – 2.38 (m, 4H), 1.61 (s, 9H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,14320-38-8, Cyclopent-3-enol, and friends who are interested can also refer to it.
Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LYSSIKATOS, Joseph P.; LIU, Wen; SIU, Michael; ESTRADA, Anthony; PATEL, Snahel; LIANG, Guibai; HUESTIS, Malcolm; CHEN, Kevin; WO2015/91889; (2015); A1;,
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