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Alkylation of CH-Acids with 3-Halomethyl Derivatives of Ethyl (Diethoxyphosphorylmethyl)furoates

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Abstract

Alkylation at the carbon atom of the active methylene group of 3-halomethyl derivatives of phosphonocarboxylic acid esters of the furan series with acetylacetone, acetoacetic, malonic and cyanoacetic esters in an absolute ethanol–dioxane medium (1 : 10) in the presence of sodium ethylate leads to the formation of the corresponding monoalkyl derivatives. The obtained phosphonomethylated derivatives of 3-(furylmethyl)acetylacetone and ethyl 2-(furylmethyl)acetoacetate react with hydrazine hydrate to form phosphorus-containing derivatives of (furyl)(pyrazolyl)methanes and (furyl)(pyrazolonyl)methanes, respectively. The latter in chloroform exist exclusively in enol form.

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REFERENCES

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Funding

The work was carried out with the financial support of Russian fund of fundamental research (grant no. 19-08-01232) within the frames of state project of ministry of education and science of Russia (project no. 785.00X6019) using the equipment of Engineering center of St. Petersburg State Institute of Technology (Technical University).

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    L. M. Pevzner, V. S. Zavgorodnii & A. I. Ponyaev

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  1. L. M. Pevzner
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  2. V. S. Zavgorodnii
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  3. A. I. Ponyaev
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Correspondence to L. M. Pevzner.

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Pevzner, L.M., Zavgorodnii, V.S. & Ponyaev, A.I. Alkylation of CH-Acids with 3-Halomethyl Derivatives of Ethyl (Diethoxyphosphorylmethyl)furoates. Russ J Gen Chem 90, 2068–2079 (2020). https://doi.org/10.1134/S1070363220110092

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  • DOI: https://doi.org/10.1134/S1070363220110092

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