Trifluoroacetic anhydride → HCID 86738421, compound

Participants

Reaction Steps

A mixture of 13.0 g (0.05 mole) of linolenic acid and 12.6 g (0.06 mole) of trifluoroacetic anhydride is stirred at room temperature for 1 hour. To the mixture 9.0 g (0.05 mole) of ethyl 3-(2-furanyl)-2-butenoate is added and the mixture is cooled and stirred at -10° C. To the mixture 5 drops of 70% perchloric acid is added and the mixture stirred at 0° C. for 3 hours. The mixture is diluted with 200 ml of ether and combined with 200 ml of saturated aqueous sodium carbonate. The layers are separated and the ether layer is washed with water, brine and evaporated to dryness. The residue is distilled under high vacuum to give ether 3-[5-(1-oxo-9,12,15-octadecatrienyl)-2-furanyl]-2-butenoate, which ester is dissolved in 300 ml of anhydrous ethanol and the solution is cooled on an ice-bath. To the mixture 14.6 g (0.2 mole) of diethylamine is added and the mixture allowed to warm up to room temperature and stand for 3 days. The reaction mixture is evaporated to dryness to give N,N-diethyl-3-[5-(1-oxo-9,12,14-octadecatrienyl)-2-furanyl]-2-butenamide.

Provenance & Evidence