Removal of Acyl Protecting Groups Using Solid NaOH and a Phase Transfer Catalyst

R. David Crouch*, Jennifer S. Burger, Karolina A. Zietek, Amy B. Cadwallader, James E. Bedison, Magda M. Smielewska

*Department of Chemistry, Dickinson College, Box 1773, Carlisle, PA 17013-2896, USA, Email: crouchdickinson.edu

R. D. Crouch, J. S. Burger, K. A. Zietek, A. B. Cadwallader, J. E. Bedison, M. M. Smielewska, Synlett, 2003, 991-992.

DOI: 10.1055/s-2003-39309

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Abstract

Acetyl-, benzoyl- and pivoyl-protected alcohols and phenols undergo smooth deacylation in a two-phase system of powdered NaOH and Bu₄NHSO₄ in THF or CH₂Cl₂.

see article for more examples

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Key Words

protecting groups, alcohols, phase-transfercatalysis, acyl groups, deacylation, deprotection (acetic acid esters, pivalic acid esters)

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ID: J60-Y2003-1990