Tetrabutylammonium Fluoride → 6-(4-Chlorophenylsulfonyl)-6-(2-chloropyridin-3-yl)-1-hexanol

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Reaction Steps

Under ice cooling, tetrabutylammonium fluoride (a 1 mol/l tetrahydrofuran solution; 0.70 ml) was added to a tetrahydrofuran (10 ml) solution of 3-[6-(tert-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine (294 mg, 0.585 mmol). The resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (212 mg, 93%) was obtained as a colorless oil.

Provenance & Evidence