4,5-Anhydro-1,3-dideoxy-4-methyl-3-prop-2-en-1-ylpent-2-ulose → 2,4-Dimethyl-3-(prop-2-en-1-yl)furan

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Reaction Steps

3-Allyl-4-methyl-4,5-epoxy-pentan-2-one (4.50 g) was added to a 1% aqueous sodium carbonate solution (150 ml), followed by stirring for 2 hours at a bath temperature of 60° to 65° C. The reaction solution was extracted three times with methylene chloride, and the methylene chloride layer was washed with an aqueous sodium chloride solution. After removing the solvent by evaporation, the residue was column chromatographed on silica gel (50 g) and developed with methylene chloride. From the first eluate (400 ml) was obtained 1.80 g of a pure objective 2,4-dimethyl-3-allylfuran.

Provenance & Evidence