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

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%).

1. customwas returned to room temperature
2. extractionThen, the reaction mixture was extracted with ethyl acetate
3. additionafter the addition of a saturated ammonium chloride aqueous solution
4. washThe ethyl acetate layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. customevaporated
7. customThe crude product was purified by column chromatography (12 g, 2% AcOEt-hexane)

ORD record

ord-8336cfa63dbe42869d92cd60c664556d

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982257B1