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Synthesis of Propargyl (±)-(5-Methylidene-4-oxopent-2-en-1-yl)Acetate

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Abstract

The synthesis of propargyl (±)-(5-methylidene-4-oxocyclopent-2-en-1-yl)acetate from a methoxycarbonyl precursor is described. The synthesis includes the stages of formation of a Michael adduct with thiophenol at the terminal double bond, Luche reduction of the keto group, alkaline hydrolysis of the ester function, and alkylation of the acid with propargyl bromide to obtain carboxy-protected cyclopentenol. The latter is converted into ketosulfone by oxidation with the Dess–Martin reagent and then by treatment with 30% hydrogen peroxide. The elimination of PhSO2H from ketosulfone leads to the target molecule.

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ACKNOWLEDGMENTS

The work was performed using the equipment of the Chemistry Center for Collective Use, Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The work was performed according to the state assignment nos. AAAA-A17-117011910032-4 and AAAA-A17-117011910027-0.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Z. R. Makaev, N. S. Vostrikov & M. S. Miftakhov

Authors
  1. Z. R. Makaev
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  2. N. S. Vostrikov
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  3. M. S. Miftakhov
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Correspondence to Z. R. Makaev.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 11, pp. 1207–1213 https://doi.org/10.31857/S051474922211009X.

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Makaev, Z.R., Vostrikov, N.S. & Miftakhov, M.S. Synthesis of Propargyl (±)-(5-Methylidene-4-oxopent-2-en-1-yl)Acetate. Russ J Org Chem 58, 1623–1627 (2022). https://doi.org/10.1134/S1070428022110094

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  • DOI: https://doi.org/10.1134/S1070428022110094

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