Benzyl Bromide → (2R,3R)-3-(Benzyloxy)butan-2-OL

Participants

Reaction Conditions

Reaction Steps

A solution of (2R,3R)-butane-2,3-diol in THF was admixed at room temperature with potassium tert-butylate and the mixture was refluxed for 15 minutes. The mixture was cooled to ca. 50° C. and admixed with benzyl bromide. The mixture was refluxed for 3 hours, then stirred overnight at room temperature. The mixture was diluted with acetic ester and sodium chloride solution and then washed with 1 N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified by means of chromatography (hexane/acetic ester 1:1) (yield: 43%).

Provenance & Evidence