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Synthesis 2011(13): 2159-2164  
DOI: 10.1055/s-0030-1260034
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Mild and Efficient Protocol for the Protection of 3-Hydroxychromones Under Phase-Transfer Catalysis

Dmytro Dziuba, Rachid Benhida, Alain Burger*
Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR 6001 CNRS, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, 28 avenue de Valrose, 06108 Nice Cedex 2, France
Fax: +33(4)92076151; e-Mail: burger@unice.fr;
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Publication History

Received 7 March 2011
Publication Date:
06 May 2011 (online)

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Abstract

A mild and efficient protocol for the introduction of different protecting groups on 3-hydroxychromones (3-HCs) under phase-transfer catalysis conditions in toluene or dichloromethane/aqueous potassium hydroxide system in the presence of crown ether has been developed. The method is useful for the protection of base-sensitive chromone derivatives. Protected chromones are easier to handle and to purify, and therefore suitable for further chemical transformations. The protecting groups were cleaved cleanly using standard conditions.

Key words

3-hydroxychromone - phase-transfer catalysis - protecting groups - acylation - alkylation - cleavage

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