Phenacyl bromide → HCID 117761577, compound

Participants

Reaction Steps

To a solution of (1R,2S,3S,4R,55)-1-(acetoxymethyl)-5-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (260 mg, 0.46 mmol) and DIPEA (0.38 mL, 2.25 mmol) in acetonitrile (2.25 mL), 2-bromo-1-phenylethanone (269 mg, 1.3 mmol) was added at r.t. and stirred overnight. After completion of the reaction as confirmed by TLC, the reaction mixture was diluted with ethylacetate (100 mL) and washed with water (20 mL) and brine (20 mL) successively. The organic layer was dried over Na2SO4 and the volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 2.2:7.8 acetone:hexane) to afford the title compound (230 mg, 0.33 mmol, 73.6%).

Provenance & Evidence