A Synthesis of Furans from Epoxycarbonyl Precursors

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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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