Volume 23, Issue 32
Preparative Organic Chemistry
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ChemInform Abstract: Cyanomethyl Esters: Useful Protection for Carboxylic Acids.

H. M. HUGEL

H. M. HUGEL

Dep. Appl. Chem., Phillip Inst. Technol., Bundoora, Victoria 3083, Australia

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K. V. BHASKAR

K. V. BHASKAR

Dep. Appl. Chem., Phillip Inst. Technol., Bundoora, Victoria 3083, Australia

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R. W. LONGMORE

R. W. LONGMORE

Dep. Appl. Chem., Phillip Inst. Technol., Bundoora, Victoria 3083, Australia

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First published: August 11, 1992

Abstract

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ChemInform Abstract

Carboxylic acid cyanomethyl esters are hydrolyzed under very mildly basic conditions using Na2S or a K2CO3/KHCO3 mixture in aqueous acetone. As the cyanomethyl esters can be prepared from the carboxylic acids without prior activation, their formation and subsequent cleavage represent an effective method for the protection of even sterically hindered carboxylic groups in acid-sensitive compounds such as gibberellic acid (IVa) and 3-epi-gibberellic acid (IVb).

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