Ethyl 2-chloroacetoacetate → HCID 19965125, compound

Participants

Reaction Conditions

Reaction Steps

390 mg of 3-Isopropoxythiobenzamide was dissolved in 5 ml of ethanol, 360 mg of ethyl 2-chloroacetoacetate was added to the solution, and the mixture was heated under reflux for five hours. After the reaction mixture was cooled, it was concentrated and subjected to silica gel chromatography (eluent, hexane: ethyl acetate=9:1) to separate an intended product (490 mg). The resulting oily substance was dissolved in 5 ml of ethanol, 10 ml of a 1N aqueous sodium hydroxide solution was added, and the mixture was heated at 70° C. for one hour. After the completion of the reaction, ethanol was removed by distillation and the residue was neutralized with 1N hydrochloric acid. The precipitated crystal was collected by filtration and recrystallized from a 50% aqueous ethanol solution to give 358 mg of 2-(3-isopropoxyphenyl)-4-methyl-5-thiazolecarboxylic acid (yield: 65%).

Provenance & Evidence