Water → Methyl 3-oxovalerate

Participants

Reaction Steps

116 g of acetoacetic acid methyl ester and 75 g of pyrrolidine were boiled in 350 ml of toluene on a water separator until the theoretical quantity of water was separated. The solution was added drop by drop at -40° C. to a suspension of 47 g of sodium amide in 800 ml of liquid ammonia. The ammonia was removed by allowing the temperature of the reaction solution to rise to -20° C., and then, at such temperature, a solution of 114 g of methyl bromide in 500 ml of toluene was added drop by drop. The reaction solution was filtered and the toluene was removed using a rotary evaporator. The residue, after the addition of 700 ml of methylene chloride and 102 g of concentrated hydrochloric acid thereto, was hydrolyzed for 1 hour at ambient temperature. The two phases were separated, the organic phase was dried and the solvent was removed. 120 g of 3-oxopentanoic acid methyl ester (92 percent) was obtained.

Provenance & Evidence