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Synthesis and some transformations of diethyl (5-trifluoromethylfur-2-yl)methanephosphonate

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Abstract

By the interaction of 2-bromomethyl-5-trifluoromethyfuran with triethyl phosphite under the Arbuzov reaction conditions diethyl (5-trifluoromethylfur-2-yl)methanephosphonate was prepared. Due to deactivation of the furan ring this substance does not enter chloromethylation even at 70°C. Because of CH-acidity of the diethoxyphosphorylmethyl fragment diethyl (5-trifluoromethylfur-2-yl)methanephosphonate in the presence of sodium foil enters the Claisen reaction with ethyl formate and diethyl oxalate. Respective derivatives of furylacetaldehyde and furylpyruvic acid and their sodium salts were isolated and characterized. Reactions of the compounds obtained with methyl iodide and diethyl chlorophosphate were studied. It was shown that trifluoromethyl derivative of phosphorylated furylacetaldehyde forms stable enol ethers and esters. The furylpyruvic acid derivative is alkylated with methyl iodide at the carbon atom adjacent to phosphorus and the compound formed undergoes cleavage to 1-(5-trifluoromethylfur-2-yl)ethanephosphonate.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute, Technical University, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    L. M. Pevzner

  2. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. L. M. Pevzner
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  2. V. A. Polukeev
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Correspondence to L. M. Pevzner.

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Original Russian Text © L.M. Pevzner, V.A. Polukeev, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 9, pp. 1542–1550

To the 85th Anniversary of birthday of late Yu.G. Gololobov

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Pevzner, L.M., Polukeev, V.A. Synthesis and some transformations of diethyl (5-trifluoromethylfur-2-yl)methanephosphonate. Russ J Gen Chem 85, 2120–2127 (2015). https://doi.org/10.1134/S1070363215090169

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  • DOI: https://doi.org/10.1134/S1070363215090169

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