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

Participants

Reaction Conditions

Reaction Steps

A solution of 4.0 g (44.4 mmol) of (2R,3R)-butane-2,3-diol in 300 ml of THF was admixed at room temperature with 5.0 g (44.6 mmol) of potassium tert-butylate and the mixture was refluxed for 15 minutes. The mixture was cooled to ca. 50° C. and admixed with 5.3 ml (44.6 mmol) of benzyl bromide. The mixture was refluxed for 3 hours, then stirred overnight at room temperature. The mixture was diluted with ethyl acetate and sodium chloride solution and then washed with 1N hydrogen chloride solution (1×) and sodium chloride solution (2×). The organic phase was dried (Na2SO4), filtered and concentrated by evaporation. The resulting residue was purified chromatographically (hexane/ethyl acetate 1:1). This gave 3.4 g (18.9 mmol; yield: 43%) of the product.

Provenance & Evidence