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Synthesis of Isomeric (Methoxycarbonyl)furoyl Phosphonates and Their Reaction with Ethoxycarbonylmethylenetriphenylphosphorane

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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.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190031, Russia

    L. M. Pevzner

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  1. L. M. Pevzner
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Correspondence to L. M. Pevzner.

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Original Russian Text © L.M. Pevzner, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 6, pp. 943–951.

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Pevzner, L.M. Synthesis of Isomeric (Methoxycarbonyl)furoyl Phosphonates and Their Reaction with Ethoxycarbonylmethylenetriphenylphosphorane. Russ J Gen Chem 88, 1124–1132 (2018). https://doi.org/10.1134/S1070363218060130

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  • DOI: https://doi.org/10.1134/S1070363218060130

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