Acetone → HCID 68716253, compound

Participants

Reaction Steps

A solution of 4.9 g (14.8 mmol) of the product of Step A in 30 mL of CH2Cl2 was placed in an external cooling bath containing dry ice and acetone and stirred under a nitrogen atmosphere. A 1.0 M solution of boron tribromide (20 mL, 20.0 mmol) in CH2Cl2 was added dropwise. After the addition was complete, the reaction mixture was stirred an additional 5 min then allowed to warn to room temperature. After stirring 1 h the reaction mixture was poured into 500 mL ice water and was stirred for 30 min. The aqueous layer was separated and extracted with 100 mL CH2Cl2. The organic layers were combined, dried Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 3% EtOAc-hexanes. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Provenance & Evidence