m-Chloroperbenzoic acid → (3S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene oxide

Participants

Reaction Steps

Under argon atmosphere, (S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene (50) (1.0 g, 3.1 mmol) was dissolved in 25 ml of dry dichloromethane, mCPBA (1.4 g, 7.4 mmol) was added to the resultant solution at 0° C., and the mixture was stirred for 15 min. Then, the mixture was further stirred overnight after the temperature was returned to room temperature. The reaction mixture was extracted with ethyl acetate after the addition of water. The ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated. The obtained crude product was purified by column chromatography (30 g, 2% Et2O-hexane) to obtain a colorless oily product (51). (1.1 g, quant.).

Provenance & Evidence