The Preparation ofN-Acylpyrazoles and Their Behavior Toward Alcohols

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Abstract
According to four different methods, various types of N-acylpyrazoles were prepared from the corresponding pyrazoles and carboxylic acids or their acid chlorides. Although N-acylpyrazoles were inert to alcohols under neutral or weakly basic conditions, the alcoholysis was dramatically accelerated by the action of strong acid or base. On the basis of these chemical properties, the regioselective synthesis of methyl benzyl 2,2-dimethylglutarate was achieved by selective protection and functionalization of a carboxylic acid derivative using N-acylpyrazoles.

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