Boron tribromide → HCID 58604056, compound

Participants

Reaction Steps

A solution of 8a-butyl-6-methoxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (37 mg, 0.14 mmol) in anhydrous CH2Cl2 (1.4 mL) was placed under a nitrogen atmosphere, cooled in a dry ice-acetone bath, and treated over two minutes with 1M BBr3 in CH2Cl2 (0.42 mL, 0.42 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for 3 hours. Additional 1M BBr3 in CH2Cl2 (0.1 mL, 0.1 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was partitioned between EtOAc and aqueous 1N HCl. The organic phase was washed with 5% NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum to provide a solid residue. Recrystallization of this material from hot EtOAc gave pure 8a-butyl-6-hydroxy-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (11 mg). Concentration of the mother liquors gave additional product contaminated with ˜5% of starting material.

Provenance & Evidence