Sodium hydride → HCID 19790985, compound

Participants

Reaction Steps

5.0 g (20 mmol) of benzylmalonic acid diethyl ester were added dropwise at room temperature to a suspension of 0.87 g of sodium hydride dispersion (55% in oil) in 20 ml of dimethylformamide. Subsequently, the reaction mixture was stirred at room temperature for 20 minutes and thereafter 4.67 g (20 mmol) of omega-bromo-4-chloroacetophenone in 25 ml of dimethylformamide were added dropwise. After completion of the addition, the deep brown colored reaction mixture was stirred at room temperature overnight and thereafter evaporated in a high vacuum. The residue was dissolved in methylene chloride, washed with water and dried over sodium sulfate. Thereafter, the solvent was evaporated under reduced pressure and the residue, for purification, was chromatographed on silica gel with a 6:1 mixture of hexane and ether, to obtain 5.17 g (64%) of 2-(RS)-benzyl-2-carbethoxy-4-(4-chloro-phenyl)-4-oxobutyric acid as a yellowish solid. MS: 357 (M-OC2H5)+, 311 (M-benzyl)+.

Provenance & Evidence