Triethylamine → 4,4,5,5,5-Pentafluoropentyl thioacetate

Participants

Reaction Steps

To a solution of 4,4,5,5,5-pentafluoropentanol (23.2 g, 130 mmol) in dry dichloromethane (100 ml) were added dropwise at 0° C. triethylamine (27 g, 267 mmol) and methanesulfonylchloride (30 g, 262 mmol), which was then warmed to room temperature over 12 hours. After the reaction was completed, the mixture was poured into ice-water, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product (33.9 g). This crude product thus obtained was then dissolved in acetone (500 ml), potassium thioacetate (18 g, 158 mmol) was added thereto at room temperature, and the resulting mixture was stirred for 12 hours. The precipitate was filtered, and the filtrate was concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give 4,4,5,5,5-pentafluoropentylthioacetate (15.8 g, yield 51%).

Provenance & Evidence