Preparation of gamma-pyrones from 3-substituted furans

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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C07D30922

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041735722

ABSTRACT:
Gamma-pyrones are prepared by contacting a 3-halo-furfuryl alcohol or a 3-alkoxy-furfuryl alcohol with one equivalent of a halogen, peracid or peroxide oxidant and then heating until hydrolysis of the formed 4-substituted-dihydropyran intermediate is substantially complete. Maltol (2-methyl-3-hydroxy-4H-pyran-4-one) is prepared by this process from 2(1-hydroxyethyl)-3-alkoxy furans or 2(1-hydroxyethyl)-3-halo-furans. Gamma-pyrones are also prepared by contacting the corresponding 3-substituted-2,5-dialkoxy-furfuryl alcohols with acid until conversion to the gamma-pyrones is substantially complete.

REFERENCES:
Shono et al., Tetrahedron Letters, 17, 1363 (1976).
Laliberte et al., J. Med. Chem., 16, 1084 (1973).
Achmatowicz, Jr. et al., Tetrahedron, 32, 1051 (1976).
Achmatowicz, Jr. et al., Tetrahedron, 27, 1973 (1971).

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