Tetrahedron

A direct and mild conversion of tertiary aryl amides to methyl esters using trimethyloxonium tetrafluoroborate: A very useful complement to directed metalation …

GE Keck, MD McLaws, TT Wager

Index: Keck, Gary E; McLaws, Mark D; Wager, Travis T Tetrahedron, 2000 , vol. 56, # 51 p. 9875 - 9883

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Citation Number: 42

Abstract

The scope and generality of a direct process for the conversion of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, ...

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