Intermediates for the preparation of gamma-pyrones

Details Intermediates for the preparation of gamma-pyrones Intermediates for the preparation of gamma-pyrones

1981-10-14

1983-06-07

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30922

Patent

active

043872352

ABSTRACT:
2-methyl-3-hydroxy-4H-pyran-4-one is prepared by contacting 1(2-furyl)-1-ethanol in aqueous solution with two equivalents of a halogen oxidant at room temperature and then heating until the hydrolysis of the formed 4-halo-dihydropyran intermediate is substantially complete. Other valuable related gammapyrones are prepared in analogous manner from appropriate alcohols.

REFERENCES:
patent: 3707482 (1972-12-01), Laliberte
patent: 3751434 (1973-08-01), Lefebvre
patent: 4173572 (1979-11-01), Brennan et al.
Schenck et al., J. Am. Chem. Soc. 67, 2276 (1945).
Spielman et al., J. Am. Chem. Soc., 69, 2908 (1947).
Chawla et al., J. Org. Chem., 39, 3281 (1974).
Lichtenthaler et al., Angew Chem. Int. Ed., 8, 978 (1969).
Torii et al., Chemistry Letters No. 5, 495 (1976).
Hajivarnava, Carb. Res. 49, 93 (1976).
Paulsen et al., Tetrahedron Letters, No. 2, 133 (1972).

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