Tetrahedron p. 5095 - 5100 (1988)
Update date:2022-08-05
Topics:
Saalfrank, R. W.
Hafner, W.
Markmann, J.
Bestmann, H.-J.
Starting from enolizing 1,2-diketones 5 and (2,2-diethoxyvinylidene)triphenylphosphorane (2) or from 5 and (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborate (6) the orthoesters 9 are prepared. 9 can be hydrolyzed under acidic conditions to give 5-alkylidene-2(5H)-furanones 10.Reaction of 1,2-hydroxyketones 11 and (2,2-ditehoxyvinylidene)triphenylphosphorane (2) via Michael addition and Wittig reaction yields orthoesters 15, which can be hydrolyzed to give 2(5H)-furanones 16 and 2-ethoxyfurans 17 respectively.A considerable variation of the substitens (R4)can be achieved starting from 11 and (2,2-diethoxyvinyl)triphenylphosphonium tetrafluoroborates 12.
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