Pyridine → Ethyl 2-methylsulfonyloxypropanoate

Participants

Reaction Steps

24.11 G (0.2041 mol) of ethyl L-(+)-lactate and 50 ml of anydrous pyridine were stirred in an ice bath. 17.0 Ml (25.2 g, 0.220 mol) of methanesulfonyl chloride was added dropwise over a period of 20 minutes, and the mixture was stirred for 1 hour at the same temperature and for 1 hour at room temperature. 200 Ml of water was added, and extraction was performed with methylene chloride (50 ml, 3 times). The extract was washed with water (50 ml), then dried with anhydrous magnesium sulfate, and vacuum concentrated. The red-colored oily residue was vacuum distilled, and 32.20 g of ethyl (-)-2-methanesulfonyloxypropionate was obtained in the form of a colorless liquid with bp 97°-102° C./2 Torr. Yield 82.0%.

Provenance & Evidence