Acetic Acid → HCID 57545194, compound

Participants

Reaction Steps

1.2 ml of glacial acetic acid are added to 814 mg (3.09 mmol) of tetramethylammonium triacetoxyborohydride in 1.2 ml of acetonitrile under argon, and the mixture is stirred at RT for 0.5 h. Then 105 mg (0.21 mmol) of (3S*,3aR*,8bR*)-3a-(4-bromophenyl)-6,8-diethoxy-8b-hydroxy-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1-one are added dropwise as solution in 12 ml of acetonitrile. The mixture is stirred at RT overnight. At 0° C., saturated sodium bicarbonate solution is added to the reaction mixture, the aqueous phase is extracted twice with dichloromethane, and the combined organic phases are dried over sodium sulfate, filtered and concentrated. Gradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 77 mg (71% of theory) of the product as racemic mixture.

Provenance & Evidence