A Novel Synthesis of Esters via Substitution of the Benzotriazolyl Group in 1-(Benzotriazol-1-yl)alkyl Esters with Organozinc Reagents

Abstract

Aldehydes are converted by thionyl chloride and benzotriazole into 1-(1-chloroalkyl)benzotriazoles which react with sodium carboxylates to give 1-(benzotriazol-1-yl)alkyl esters 3. In an alternative route, 3 are prepared by substitution of one of the acetoxy groups in acylals with benzotriazole. The benzotriazolyl moiety in 3 is substituted by an alkyl, an aryl or an alkynyl group upon treatment with an organozinc reagent in a new versatile synthesis of esters 4.