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Updated: Jun 18, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Cyclic Acetal Formation Between 2-Pyridinecarboxaldehyde and gamma-Hydroxy-alpha,beta-Acetylenic Esters
1Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260.
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A new transformation between 2-pyridinecarboxyaldehyde and gamma-hydroxy-alpha,beta-acetylenic esters to form highly functionalized cyclic acetals was discovered. This transformation proceeds under very mild conditions without any additives and is promoted by the basic nature of the pyridine ring.
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During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...