Furan → 1-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne

Participants

Reaction Steps

To a mixture of 6-methoxycarbonyl-1-carboxy-3-hexyne [VI-1] (27.6 g, 0.15 mole), furan (30.7 g, 0.45 mole) and dichloromethane (150 ml) is added trifluoroacetic anhydride (37.8 g, 0.18 mole) at room temperature, and the mixture is reacted at 30°-35° C. for 24 hours. After completion of the reaction, the reaction solution is poured into ice-water and neutralized with 20% aqueous sodium hydroxide solution. The organic layer is separated and washed successively with 5% aqueous sodium hydrogen carbonate solution and water. The organic layer is concentrated under reduced pressure to give 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (32.3 g, yield; 92%).

Provenance & Evidence