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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 7
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Original Articles

A Synthesis of Furans from Epoxycarbonyl Precursors

, &
Pages 677-679 | Published online: 19 Dec 2006
 

Abstract

Following our study of the preparation of 2-ethyl-4-methylfuran (2a) by rearrangement of 5-methyl-5,6-epoxy-3-hexanone (1a),1 we undertook an investigation of the conversion of other epoxycarbonyl precursors to furans in order to determine the scope and utility of this transformation. The transformations examined in the present study are shown below. The epoxycarbonyl substrates were conveniently prepared from commercially available unsaturated alcohols by first expoxidation with m-chloroperoxybenzoic acid followed by oxidation with chromium trioxide-pyridine reagent in methylene chloride solution.2

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