Diethyl Malonate → HCID 11984308, compound

Participants

Reaction Conditions

Reaction Steps

At room temperature, 28.9 g of sodium methoxide (95% pure, 0.51 mol) were dissolved in 150 ml of dry methanol under protective nitrogen gas in a three-neck flask with internal thermometer, dropping funnel and stirrer. Subsequently, 85.3 g of diethyl malonate (0.533 mol) were added dropwise at from 30 to 35° C., in the course of which a suspension initially formed and dissolved toward the end of the addition. The clear mixture was stirred at 50° C. for 60 min and 80 g of (S)-1-methylpentyl methanesulfonate (0.444 mol) were added undiluted. The mixture was heated to 66° C. and stirred for 6 h. After cooling to 25° C., the suspension was admixed with 400 ml of methylene chloride and 300 ml of 5% by weight ammonium chloride solution. After phase separation, the organic phase was washed with 100 ml of water and then dried over sodium sulfate. After distillative removal of solvent, diethyl [(R)-1-methylpentyl]malonate was obtained in a yield of 94 g. The product comprises dimethyl ester and ethyl methyl ester, formed by transesterification, and unconverted malonic ester. The corrected yield is 84% of theory.

Provenance & Evidence