Triethylamine → (+)-Glycidol

Participants

Reaction Steps

One gram of (R) or (S)-glycidol was dissolved in 20 ml of anhydrous toluene, and 2 ml of triethylamine was added. The mixture was cooled with ice, and 2.79 g of o-nitrobenzenesulfonyl chloride was added with stirring in three portions at an interval of 10 minutes. The mixture was further stirred for 1 hour with ice cooling. After the reaction, the insoluble materials were removed by filtration. The filtrate was concentrated at below 30° C., and the residue was charged onto a column of silica gel. The column was developed with benzene/ethyl acetate (10/1) to give 1.9 g of (S)-compound from (R)-glycidol, and 2.54 g of (R)-compound from (S)-glycidol.

Provenance & Evidence