Antimony(V) Chloride as an Efficient Reagent for Deprotection of Methyl Ethers

Fariba Saadati; Hamid Meftah-Booshehri

doi:10.1055/s-0033-1339310

Synlett, Table of Contents

Synlett 2013; 24(13): 1702-1706
DOI: 10.1055/s-0033-1339310

letter

Antimony(V) Chloride as an Efficient Reagent for Deprotection of Methyl Ethers

Fariba Saadati*

Department of Chemistry, Faculty of Science, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran Fax: +98(241)2283203 Email: saadati@znu.ac.ir

,

Hamid Meftah-Booshehri

Department of Chemistry, Faculty of Science, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran Fax: +98(241)2283203 Email: saadati@znu.ac.ir

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Abstract

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Abstract

This paper proposes a new and efficient method for the deprotection of methyl ethers using antimony pentachloride at ambient temperature. The procedure described here is a facile and practical method for the removal of the methyl group from aryl and benzyl methyl ethers. High selectivity was observed for the removal of the methyl group from dimethoxyarenes. The notable advantages of this protocol are mild reaction conditions, high yields, and the facility of workup procedure. The mechanism of the ether cleavage is proposed to explain this new reaction.

Key words

demethylation - methyl ether - antimony pentachloride - selectivity - dimethoxyarenes

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References

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