反应详情

To a suspension of NaH (153 mg 60% dispersed in mineral oil, 6.39 mmol) in 20 mL THF was slowly added at room temperature 4-(tert-butyl-diphenyl-silanyloxy)-1-(4-chloro-phenyl)-butan-1-ol (330 mg, 0.75 mmol) as a solution in 10 mL THF followed by the dropwise addition of methyl iodide (339 μL, 5.25 mmol). The reaction mixture was stirred for 3 h at room temperature before being quenched by the careful addition of saturated aqueous NH4Cl (30 mL). The mixture was extracted with ethylacetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. After evaporation of solvent the product was isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give 343 mg of the title compound as a colorless oil.

1. custombefore being quenched by the careful addition of saturated aqueous NH4Cl (30 mL)
2. extractionThe mixture was extracted with ethylacetate (3×30 mL)
3. washthe combined organic layers washed with brine (2×20 mL)
4. dry with materialdried over sodium sulfate
5. customAfter evaporation of solvent the product
6. customwas isolated by flash column chromatography
7. washeluting with 0% to 30% ethyl acetate/hexane