Methanol → 7-Carbomethoxy-benzopyran-4-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7-trifluoromethylsulfonyloxy-benzopyran-4-one (7.89 g, 26.6 mmole) in DMF (54 ml) was added methanol (21.6 ml), palladium acetate (110 mg, 0.533 mmole), DPPF (590 mg, 1,066 mmole) and triethylamine (7.477 ml, 53.3 mmole). Carbon monoxide gas was bubbled through the solution for 5 minutes, and the mixture was stirred at 50° C. for 3 hours under 1 atmosphere of CO. After cooling, the mixture was poured into 120 ml of 1M sulfuric acid and extracted with 2×75 ml of ethylacetate. The combined organic fractions were washed with brine, dried over MgSO4, and filtered. Solvent evaporation in vacuo and chromatography (silica gel 1:1 hexane:ether) gave 5.19 g of the title compound (94% yield).

Provenance & Evidence