Acetic Acid → HCID 19434001, compound

Participants

Reaction Conditions

Reaction Steps

The product from Step B (4.20 g, 12.14 mmol) was dissolved in THF (40 mL) containing 30% HBr in acetic acid (0.1 equiv, 0.25 mL) and cooled to 3° C. A solution of pyridinium bromide perbromide (4.32 g, 13.52 mmol) in THF (20 mL) was added and the reaction mixture allowed to warm to room temperature. The THF was evaporated and the residue dissolved in ethanol (40 mL); this solution was cooled (3° C.), sodium borohydride (pellets, 3.25 g, 86.03 mmol) added and the reaction mixture stirred at 5° C. for 1 hr followed by heating at reflux temperature for 1 hr. The reaction mixture was evaporated to a residue which was suspended in water and the pH of this suspension was adjusted to 7 with saturated aqueous ammonium chloride. This mixture was extracted with ethyl acetate (3×50 mL) and the combined extracts were dried (MgSO4). The products from two such reactions were purified by column chromatography (silica gel, 1:1 ethyl acetate/hexane) to give the desired product (3.6 g), mp 127°-132° C.; this material was used in the next reaction.

Provenance & Evidence