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Condensation of 3,5-Dialkyltetrahydro-4H-thiopyran-4-ones with Formaldehyde

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Abstract

The reaction of 3,5-dimethyl- and 5-methyl-3-(2-propyl)tetrahydro-4H-thiopyran-4-ones with formaldehyde without or in the presence of 0.1–0.5 equiv. sodium hydroxide produces 3,5-dialkyl-3-(hydroxymethyl)tetrahydro-4H-thiopyran-4-ones. 3,5-Dimethyltetrahydro-4H-thiopyran-4-one converted into 3,5-bis(hydroxymethyl)tetrahydro-2H-thiopyran-4-ol when the amount of base to 1 equiv increase. Under similar conditions 5-methyl-3-(2-propyl)tetrahydro-4H-thiopyran-4-one form 3-hydroxymethyltetrahydro-2H-thiopyran-4-ol, which cyclization to 7-oxa-3-thiabicyclo[4.2.0]octane.

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ACKNOWLEDGMENTS

Spectral and analytical results were obtained using the equipment of the Center for Collective Use “Chemistry” of the Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences.

Funding

The work was carried out within the framework of the state task (subject no. 122031400274-4).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Researcher Centre of the Russian Academy of Sciences, 450054, Ufa, Russia

    L. A. Baeva, L. F. Biktasheva, R. R. Gataullin & A. A. Fatykhov

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  1. L. A. Baeva
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  2. L. F. Biktasheva
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  3. R. R. Gataullin
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  4. A. A. Fatykhov
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Correspondence to L. A. Baeva.

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Baeva, L.A., Biktasheva, L.F., Gataullin, R.R. et al. Condensation of 3,5-Dialkyltetrahydro-4H-thiopyran-4-ones with Formaldehyde. Russ J Gen Chem 92, 1677–1685 (2022). https://doi.org/10.1134/S1070363222090092

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