Triphenylphosphine → 3-Methyl-4-(5-fluorobenzofur-7-yl)pentan-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 gm (4.65 mMol) 5-fluoro-7-bromobenzofuran, 0.54 ml (5.23 mMol) 2-methyl-3-hydroxybut-1-ene, 9 mg (0.04 mMol) palladium(II) acetate, 0.021 gm (0.08 mMol) triphenylphosphine, and 0.44 gm (5.23 mMol) sodium bicarbonate in 5 mL hexamethylphosphoramide was heated at 130° C. for 3.5 hours. The reaction mixture was cooled to room temperature and was then diluted with 100 mL diethyl ether. The organic phase was washed sequentially with 2×20 mL water followed by 2×20 mL saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10:1 hexane:diethyl ether. Fractions containing the desired product were combined and concentrated under reduced pressure to provide the desired product in 81% yield as a colorless oil.

Provenance & Evidence