Pivaloyl chloride → HCID 19760159, compound

Participants

Reaction Steps

Pivaloyl chloride (2.070 ml, 17.1 mmol) was added slowly to a solution of 5-benzyloxy-1,3-pentanediol (39, 16.3 mmol) in anhydrous pyridine (35 ml) at -18° C. (dry ice-acetone bath). The mixture was kept without stirring in a -20° freezer for 15 hours. The reaction mixture was then diluted with methanol (1 ml) and CH2Cl2 (50 ml), and extracted with 10% HCl containing copper sulfate (10 g/l) until the blue color in the organic layer was removed. The aqueous layer was re-extracted with methylene chloride, the combined organic layers are dried (magnesium sulfate), the solvent evaporated, and 1-pivaloyloxy-5-benzyloxy-3-pentanol (40) isolated as a colorless oil by flash chromatography on silica gel (hexane/EtOAc 7:3 as eluant; yield 4.05 g, 86% as a colorless oil).

Provenance & Evidence