Synthesis of 6-methylfuro[2,3-b]pyridine

The Claisen condensation of ethyl 2-ethoxy-6-methylpyridine-3-carboxylate with ethyl acetate gave ethyl 2-ethoxy-6-methylnicotinoylacetate, which was converted to 3-bromo-acetyl-6-niethyl-2-pyridone by heating with bromine in 48% hydrobromic acid. The cyclization of the bromoacetylpyridone by the action of silver oxide in methanol gave 3-oxo-6-methyl-2,3-dihydrofuro2,3-b]pyridine, which was reduced to 3-hydroxy-6-methyl-2,3-dihydrofuro2,3-b]pyridine with lithium aluminum hydride in dimethoxyethane. Acetylation of the latter gave its acetate, the pyrolysis of which in vacuo gave 6-methylfuro2,3-b]-pyridine.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1544–1546, November, 1972.