Acetic Acid Mixture with Hydrobromic Acid → HCID 86729345, compound

Participants

Reaction Steps

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (5.5 g, 9.54 mmol), in acetic acid (23.62 mL) under nitrogen atmosphere, was added 37% HBr/AcOH (47.7 mL). The reaction mixture was stirred at r.t. for 3 h. After the completion of the reaction as confirmed by TLC, the reaction mixture was cooled to 0° C. and quenched very slowly with saturated solution of potassium carbonate until effervescence ceases. The crude compound was extracted with ethyl acetate (2×300 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford crude compound which was purified by column chromatography (silica gel, 3:7 Ethyl acetate:Pet ether) to afford the title compound (4.28 g, 79%) as a white solid.

Provenance & Evidence