Triethylamine → 4-(Methanesulfonyl)oxytetrahydrothiopyran

Participants

Reaction Steps

To a 300 ml methylene chloride solution of 14.6 g (0.12 mol) of 4-hydroxytetrahydrothiopyran, 11.5 ml (0.15 mol) of methanesulfonyl chloride and 25.8 ml (0.19 mol) of triethylamine were added at 0° C. and stirred at room temperature for 1 hour. The reaction mixture was diluted with methylene chloride (100 ml) and successively washing with water (100 ml) and saturated saline (100 ml), followed by drying over anhydrous sodium sulfate. The solvent was then distilled off under vacuum to obtain 24.5 g (quant.) of the above-identified compound as a slightly brown crystal.

Provenance & Evidence