Hydrochloric Acid → HCID 15023454, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(2-propynyl)-2-hydroxy-2,2-diphenylacetamide (165.2 g), cuprous chloride (2.50 g) and potassium carbonate (1.73 g) in dimethylsulfoxide (330 ml) was stirred at 75° C. for 45 minutes under a nitrogen atmosphere. To the reaction mixture was added paraformaldehyde (25.3 g) and the mixture was stirred at 85° C. for 5 hours. The reaction mixture was poured into the mixture of 5% hydrochloric acid and 10% aqueous solution of sodium chloride (1:5), and extracted with ethyl acetate. The extracts were washed successively with brine, 5% aqueous solution of sodium thiosulfate and brine, dried over magnesium sulfate and evaporated in vacuo. To the residue was added a mixture of diisopropyl ether and chloroform (1:1) (100 ml) and the mixture was stirred at room temperature for 30 minutes. The resulting precipitates were collected by filtration, washed with a mixture of diisopropyl ether and chloroform (1:1) and dried to give N-(4-hydroxy-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (119.7 g).

Provenance & Evidence