Water → Ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoate

Participants

Reaction Steps

A solution of diethyl 2-(6-heptenyl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (1.05 g, 2.1 mmol) in dimethyl sulfoxide (10 ml) was stirred with lithium chloride (0.18 g, 4.2 mmol) and water (0.038 ml, 2.1 mmol) for 5 hours at a temperature of 170° C. to 180° C. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40) to give ethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-8-nonenoate (0.80 g, Yield 89%).

Provenance & Evidence