Abstract
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-dihydrofuro[2,3-b]pyridine, which was reduced to 3-hydroxy-6-methyl-2,3-dihydrofuro[2,3-b]pyridine with lithium aluminum hydride in dimethoxyethane. Acetylation of the latter gave its acetate, the pyrolysis of which in vacuo gave 6-methylfuro[2,3-b]-pyridine.
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Literature cited
H. Sliva, Bull. Soc. Chim. France, 646 (1970).
N. K. Kochetkov, Dokl. Akad. Nauk SSSR, 84, 289 (1952).
P. I. Abramenko and V. G. Zhiryakov, Khim. Geterotsikl. Soedin., 1539 (1972).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1544–1546, November, 1972.