Triethylamine → Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Participants

Reaction Steps

To demonstrate that the heterogeneous distillate obtained as described hereinabove may be subsequently employed in the synthesis of aromatic sulfonate derivates of optically active glycidol, the distillate containing 84% (R)-glycidol in cumene was reacted with stoichiometric amounts of 3-nitrobenzene sulfonyl chloride and triethylamine to obtain optically pure (S)-glycidyl 3-nitrobenzene sulfonate as follows: 3-nitrobenzenesulfonyl chloride (10 g) was dissolved in toluene (100 g) and then combined with triethylamine (4.6 g). After cooling the solution to 5° C., the 84% (R)- glycidol distillate (3.96 g) was added. After 2 hours at 5° C. and 2 hours at 25° C., the reaction mixture was washed with water (100 g) to remove the triethylamine hydrochloride salt. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the bulk of the solvent removed under vacuum. On cooling to 0° C., (S)-glycidyl 3-nitrobenzenesulfonate crystallized out of solution. The crystalline derivative (8.2 g; 69% overall yield) was collected by filtration and washed with a small quantity of hexanes. The derivative had a melting point of 57°-59° C. and an optical purity of 96% e.e.

Provenance & Evidence