The Epoxyketone-Furan Rearrangement

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Abstract
In connection with our studies to find direct chemical evidence for oxirene intermediates,1 we prepared 1-phenyl-3-propyl-3,4-epoxy-1-hexanone (1). This epoxyketone was found to easily undergo rearrangement to afford 2-phenyl-4-propyl-5-ethylfuran (2) in quantitative yield. The transformation was effected by warming to 50° a benzene solution of epoxyketone 1 containing a catalytic amount of toluenesulfonic acid or by heating to 250° in the injector port of a gas chromatograph.