Water → {3-[(4-Bromophenyl)sulfonyl]propoxy}(tert-butyl)dimethylsilane

Participants

Reaction Steps

tert-Butyldimethylchlorosilane (508 mg) and diisopropylethylamine (587 μL) were added to a solution of 3-(4-bromophenylsulfonyl)propan-1-ol (784 mg) in N,N-dimethylformamide (4 mL), and the mixture was stirred at room temperature for 2.5 hours. tert-Butyldimethylchlorosilane (127 mg) and diisopropylethylamine (147 μL) were added to the reaction solution, and the mixture was stirred at room temperature for further two hours. tert-Butyldimethylchlorosilane (254 mg) and diisopropylethylamine (1.17 mL) were added to the reaction solution, and the mixture was stirred at room temperature for further 30 minutes. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→33:1→19:1→9:1) to give the title compound as a white solid (720 mg, 65%).

Provenance & Evidence