Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates
- Authors: Doronina E.P.1, Pevzner L.M.1, Polukeev V.A.2, Petrov M.L.1
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Affiliations:
- St. Petersburg Institute of Technology (Technical University)
- Institute of Experimental Medicine
- Issue: Vol 88, No 2 (2018)
- Pages: 241-250
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/221991
- DOI: https://doi.org/10.1134/S1070363218020093
- ID: 221991
Cite item
Abstract
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.
About the authors
E. P. Doronina
St. Petersburg Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
L. M. Pevzner
St. Petersburg Institute of Technology (Technical University)
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
V. A. Polukeev
Institute of Experimental Medicine
Email: pevzner_lm@list.ru
Russian Federation, St. Petersburg
M. L. Petrov
St. Petersburg Institute of Technology (Technical University)
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013