(S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanal → (S)-4-(t-butyldiphenylsilyloxy)-3-methyl-1-butene

Participants

Reaction Steps

Under argon atmosphere, Ph3P+CH3Br (2.2 g, 7.4 mmol) was suspended in 15 ml of THF, butyllithium (5.2 ml, 9.3 mmol) was added to the resultant solution at 0° C., and the mixture was stirred for 20 min. The treated mixture was added to a 15-ml THF solution of (S)-3-(t-butyldiphenylsilyloxy)-2-methylpropanal (49) (1.2 g, 3.7 mmol) at 0° C. The resultant mixture was stirred for 15 min and further for 45 min after the temperature was returned to room temperature. Then, the reaction mixture was extracted with ethyl acetate after the addition of a saturated ammonium chloride aqueous solution. The ethyl acetate layer was washed with brine, dried over magnesium sulfate, and evaporated. The crude product was purified by column chromatography (12 g, 2% AcOEt-hexane) to obtain a colorless oily product (50) (1.1 g, 92%).

Provenance & Evidence