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Synthesis 1991; 1991(1): 69-73
DOI: 10.1055/s-1991-26382
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A Novel Synthesis of Esters via Substitution of the Benzotriazolyl Group in 1-(Benzotriazol-1-yl)alkyl Esters with Organozinc Reagents

Alan R. Katritzky* , Stanislaw Rachwal, Bogumila Rachwal
  • *Department of Chemistry, University of Florida, Gainesville, FL 32611-2046, USA
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Publication Date:
17 September 2002 (online)

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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.