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Updated: Aug 1, 2025

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
The Direct Conversion of Esters to Ketones Enabled by a Traceless Activating Group
Patrick S Fier1, Riley A Roberts1, Reed T Larson1
1Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Abstract:
We report here the design and development of a method for the single-step conversion of esters to ketones with simple reagents. The selective transformation of esters to ketones, rather than tertiary alcohols, is made possible by the use of a transient sulfinate group on the nucleophile that activates the adjacent carbon toward deprotonation to form a carbanion that adds to the ester, followed by a second deprotonation to prevent further addition. The resulting dianion undergoes spontaneous fragmentation of the SO2 group upon quenching with water to reveal the ketone product.
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