Tetrabutylammonium Fluoride → 4-(4-Chloro-phenyl)-4-methoxy-butan-1-ol

Participants

Reaction Steps

To a solution of tert-butyl-[4-(4-chloro-phenyl)-4-methoxy-butoxy]-diphenyl-silane (343 mg, 0.75 mmol) in 20 mL THF was added at room temperature TBAF (7.5 mL, 7.5 mmol, 1M in THF). The mixture was stirred for 3 h and the reaction quenched by the addition of 10 mL saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate (3×15 mL) and the combined organic layers washed with brine (2×10 mL) and dried over Na2SO4. The mixture was concentrated and the product isolated by flash column chromatography eluting with 6% to 60% ethyl acetate/hexane to provide 120 mg of the title compound.

Provenance & Evidence