Diethyl Malonate → Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate

Participants

Reaction Steps

To a solution of sodium hydride (60%) (3.90 g, 96.07 mol) in tetrahydrofuran (160 ml) was added dropwise a solution of diethyl malonate (16.6 ml, 110.85 mol) under ice-cooling, which was then stirred for 30 minutes. Then, 1,1,1,2,2-Pentafluoro-5-iodopentane (21 g, 73.9 mol) was added dropwise thereto, and reaction mixture was warmed to room temperature, with stirring, for overnight. After the reaction was completed, the reaction was quenched with water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and removed by evaporation under reduced pressure. This product was purified by column chromatography on silica gel, eluting with dichloromethane:n-hexane=1:3 to afford 18.3 g of the title compound as a colorless oil. (yield: 78.4%)

Provenance & Evidence