Synthesis and Properties of (1,3-Dioxolan-2-yl)furans

Reaction of formylfurancarboxylates with excess ethylene glycol in the presence of p-toluene-sulfonic acid gives rise to (1'3-dioxolan-2-yl)furancarboxylates. Reduction of these products with lithiumaluminum hydride proceeds with preservation of the dioxolane ring. Except for 5-(1'3-dioxolan-2-yl)(hydr-oxymethyl)-2-methyl-3-furan, the obtained alcohols are unstable. Chlorides derived from them decomposeunder conditions of the Michaelis-Becker reaction, no phosphorylation products are formed. By contrast'the above-mentioned stable alcohol by treatment with thionyl chloride in the presence of pyridine is convertedto a fairly stable chloromethylfuran. The latter compound reacts with sodium diethyl phosphite in benzene to form the corresponding phosphonate that exists as a 1:4 mixture of two spectroscopically discernible conformers.