Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates
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Methods of synthesis of 4-functionalyzed (5-trifluoromethylfur-2-yl)methanephosphonates and (5-methyl-2-trifluoromethylfur-3-yl)methanephosphonate are developed. Their formylation with ethyl formate in the presence of sodium foil is studied. Spectral characteristics of tautomers of obtained derivatives of phosphonoacetic aldehyde are evaluated. It is shown that interaction of obtained formyl derivatives with ethoxycarbonylmethylenetriphenylphosphorane regardless of the structure of the furan fragment leads to 4-furylsubstituted alkyl 4-(diethoxyphosphoryl)but-3-enoate, the abnormal product of Wittig reaction.
Keywordstrifluoromethylfuranes methanephosphonates formylation tautomerism Wittig reaction
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- 5.Lyalin, V.V., Grigorash, R.V., Alekseeva, L.M., and Yagupolskii, L.M., Zh. Org. Khim. USSR, 1984, vol. 20, no. 4, p. 769.Google Scholar