Synthesis of Isomeric (Methoxycarbonyl)furoyl Phosphonates and Their Reaction with Ethoxycarbonylmethylenetriphenylphosphorane
- Authors: Pevzner L.M.1
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Affiliations:
- St. Petersburg State Institute of Technology (Technical University)
- Issue: Vol 88, No 6 (2018)
- Pages: 1124-1132
- Section: Article
- URL: https://journals.rcsi.science/1070-3632/article/view/222241
- DOI: https://doi.org/10.1134/S1070363218060130
- ID: 222241
Cite item
Abstract
Addition of diethyl- and diisopropyl hydrogen phosphites to isomeric (methoxycarbonyl)-2- and 3-furaldehydes in the presence of sodium ethylate or potassium fluoride led to the formation of the corresponding hydroxyphosphonates. When treated with DMSO-acetic anhydride mixture at room temperature these compounds were selectively oxidized to the corresponding furoyl phosphonates. 2-Methoxycarbonyl-3- furoyl phosphonate was synthesized via the Arbuzov reaction from 2-methoxycarbonyl-3-furoyl chloride and triethyl phosphite. The obtained isomeric (methoxycarbonyl)furoylphosphonates regardless of the structure of heterocyclic fragment react with ethoxycarbonylmethylenetriphenylphosphorane to give ethyl 3-(furyl)-3-(dialkoxyphosphoryl) acrylates with trans-location of phosphoryl and carbonyl groups against the double bond.
About the authors
L. M. Pevzner
St. Petersburg State Institute of Technology (Technical University)
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190031