反应详情

To a stirred suspension of 60% sodium hydride (200 mg, 5 mmol) and ethyl acetate (0.49 ml, 5 mmol) in tetrahydrofuran (25 ml) were sequentially added a solution of 1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone (European Patent Application EP470805) (590 mg, 2.5 mmol) in tetrahydrofuran (5 ml), two drops of ethanol and a solution of dibenzo-18-crown (15 mg, 0.04 mmol) in tetrahydrofuran (5 ml). The reaction mixture was refluxed for 5 h, allowed to cool to room temperature and finally quenched with aqueous 10% sulphuric acid solution (5 ml). The resulting mixture was diluted with diethyl ether, washed with saturated ammonium chloride solution, dried and concentrated under reduced pressure to yield a crude product which was purified by column chromatography (SiO2, hexane-ethyl acetate 4:1) to afford the title compound (610 mg, 86% yield) as a pale yellow oil.

1. temperatureThe reaction mixture was refluxed for 5 h
2. customfinally quenched with aqueous 10% sulphuric acid solution (5 ml)
3. additionThe resulting mixture was diluted with diethyl ether
4. washwashed with saturated ammonium chloride solution
5. customdried
6. concentrationconcentrated under reduced pressure
7. customto yield a crude product which
8. customwas purified by column chromatography (SiO2, hexane-ethyl acetate 4:1)