反应详情

To a solution of cyclopent-3-en-1-ol [cf. J. Org. Chem., 32, 4138 (1967)] (7.00 g) and benzyl bromide (10.5 ml) in dimethylformamide (35 ml) is added gradually 60% sodium hydride (in oil) (3.68 g) with stirring under ice-cooling, and the mixture is stirred at room temperature for 1.5 hour. The reaction mixture is diluted with ethyl acetate and washed with water six times. The ethyl acetate solution thus obtained is dried over anhydrous magnesium sulfate, evaporated to dryness under reduced pressure, and then purified by medium pressure liquid column chromatography (eluent; n-hexane, n-hexane:ethyl acetate--50:1, v/v) to give 4-benzyloxycyclopent-1-ene (11.22 g) as an oily substance.

1. temperaturecooling
2. stirringthe mixture is stirred at room temperature for 1.5 hour
3. washwashed with water six times
4. customThe ethyl acetate solution thus obtained
5. dry with materialis dried over anhydrous magnesium sulfate
6. customevaporated to dryness under reduced pressure
7. custompurified by medium pressure liquid column chromatography (eluent