Butyl vinyl ether → 8-Acetyl-3-(4-chlorophenyl)-7-hydroxy-2-isopropyl-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

3-(4-Chlorophenyl)-7-hydroxy-8-iodo-2-isopropyl-chromen-4-one (1.1 g, 2.5 mmol), 1,3-bis(diphenylphosphino)propane (206 mg, 0.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium carbonate (380 mg, 2.75 mmol) are mixed in N-methyl-2-pyrrolidinone (10 ml) in a 20 ml capacity microwave tube. Water (2 ml) and butyl vinyl ether (1.62 ml, 12.5 mmol) are added, the tube is sealed, and the mixture is heated at 80° C. under microwave irradiation for 45 min. The mixture is cooled to room temperature, poured into water (30 ml) and extracted with ethyl acetate (3×50 ml). The ethyl acetate extracts are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated to give a brown solid. This is purified by chromatography on silica gel using cyclohexane/ethyl acetate (6:1) as eluant to give a colourless solid.

Provenance & Evidence