Ethyl Acetate → 1-Propanol, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-2-methyl-, (R)-

Participants

Reaction Steps

Under argon atmosphere, Methyl(S)-3-(t-butyldiphenylsilyloxy)-2-metylpropionate (47) (1.0 g, 2.7 mmol) was dissolved in 50 ml of dry toluene, 1M DIBAL-H/hexane (5.7 ml, 5.7 mmol) was added to the resultant solution at 0° C., and the mixture was stirred for 15 min. Subsequently, the reaction mixture was further stirred for 45 min after the temperature was returned to room temperature. Ethyl acetate was added to the reaction mixture to decompose the excess DIBAL-H, and the resultant mixture was extracted with 0.5N HCl. 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, 4-10% AcOEt-hexane) to obtain a colorless oily product (48) (968 mg, quant.).

Provenance & Evidence