2H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)- → HCID 11694272, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of aluminum chloride (680 mg, 5.1 mmol) in dry THF (50 mL) was cooled to 0° C. under nitrogen. LAH (580 mg, 15.5 mmol) was added to the above solution and the resulting mixture was stirred for 20 min at 0° C., and then at rt for additional 20 min, and cooled down to −50° C. 4′-Hydroxyflavone (400 mg, 1.7 mmol) dissolved in 60 mL of THF was added slowly. The reaction mixture was stirred at −50° C. for 2 h and then for 2 h at rt. The reaction was quenched by careful addition of water (traces, to decompose LiAlH4) and the solvent was removed under reduced pressure. The crude product was initially purified by crystallization from MeOH, and then further purified by column chromatography (silica gel, 5-20% EtOAc/hexane) and repeated crystallization from MeOH to afford 109 mg of 4-(4H-chromen-2-yl)-phenol (29%). MS (ES) m/z: 225.10 (M+1), 149.04.

Provenance & Evidence