Preparation of gamma-pyrones from 3-substituted furans

Details Preparation of gamma-pyrones from 3-substituted furans Preparation of gamma-pyrones from 3-substituted furans

1978-08-28

1980-03-04

Chan, Nicky

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D30922

Patent

active

041916930

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:
patent: 3751434 (1973-08-01), Lefebvre
patent: 4059595 (1977-11-01), Shono et al.
patent: 4082717 (1978-04-01), Brennan et al.
Shono et al., Tetrahedron Letters, 17, 1363 (1976).
Laliberte et al., J. Med. Chem., 16, 1084 (1973).
Achmatowice, Jr. et al., Tetrahedron, 32, 1051 (1976).
Achmatowicz, Jr. et al. Tetrahedron, 27, 1973 (1971).
Torii et al., Chemistry Letters, 5, 495 (1976).

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