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

Participants

Reaction Steps

A mixture of 6-methoxycarbonyl-1-carboxy-3-hexyne [VI-1] (18.4 g, 0.1 mole), furan (13.6 g, 0.2 mole), dichloroacetic anhydride (28.8 g, 0.12 mole), boron trifluoride ether complex (3.2 g) and toluene (100 ml) is reacted at 20°-30° C. for 10 hours. After completion of the reaction, the reaction mixture is cooled and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (15.2 g), b.p. 120°-125° C./0.3 mmHg.

Provenance & Evidence