Water → Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.7 g of (R)-glycidol (0.09 mol)(optical purity: 99.4% ee) and 50 ml of water, 0.17 g of N,N-dimethylaminopyridine (0.0014 mol) and 17.2 g of p-toluenesulfonyl chloride (0.09 mol) in 50 ml of toluene, and then 18.1 g of 24% sodium hydroxide (0.11 mol) were added under stirring at 0-5° C. And the solution was stirred for one hour. After separation with a separating funnel, the organic layer was washed with 50 ml of 1% hydrochloric acid and 50 ml of water. The excess solvent was removed under vacuo. The chemical purity by HPLC and optical purity at that time were 99.5%, 99.5% ee respectively. The residue was recrystallized from isopropyl alcohol/hexane=1/1 (V/V) to give 16.1 g of (S)-glycidyl tosylate (yield 78%). Chemical purity: 99.9%, Optical purity: 99.6% ee

Provenance & Evidence