Water → HCID 57659600, compound

Participants

Reaction Steps

To a suspension of sodium hydride (215 mg, 4.92 mmol) in dimethoxyethane (3 ml) was added dropwise a solution of diethyl malonate (868 mg, 5.42 mmol) in dimethoxyethane (2 ml) in an inert atmosphere at rt. Stirring was continued for 1 h followed by the addition of a solution of 2-fluoro-3-methyl-benzylbromide (1 g, 4.92 mmol) in dimethoxyethane (15 ml). The reaction mixture was refluxed for 90 minutes, cooled again to rt and water (5 ml) was carefully added. The diemthoxyethane was removed under reduced pressure, DCM (100 ml) was added and the organic layer was washed with water (100 ml), dried over magenisum sulfate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silicagel, DCM/heptane=4/1) to give 973 mg (70%) of 2-(2-fluoro-3-methyl-benzyl)-malonic acid diethyl ester. LC-MS: tR=1.03 min; [M+H]+=283.22.

Provenance & Evidence