Water → Diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60%, 326 mg, 8.14 mmol) was added to dimethyl sulfoxide (5 ml) under argon atmosphere and cooled to 0° C. To this mixture, diethyl 2-(7-octeny)malonate (2 g, 7.40 mmol) dissolved in dimethyl sulfoxide (5 ml) was slowly added, followed by stirring for 1 hour. After cooling to 0° C., 1-iodo-5,5,6,6,6-pentafluorohexane (2.68 g, 8.88 mmol) dissolved in dimethyl sulfoxide (5 ml) was slowly added to the reaction mixture, followed by stirring for 2 hours at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20) to give diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonate (2.3 g, Yield 70%) as a colorless oil.

Provenance & Evidence