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Unusual removal of the ethylene ketal protection from 2,3-dichloro-4,4-ethylenedioxycyclopent-2-en-1-one under alkaline conditions. Simple synthesis of naturally occurring cyclopentenedione analogs

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Abstract

A reaction of 2,3-dichloro-4,4-ethylenedioxycyclopent-2-en-1-one with MeONa in MeOH to furnish 2-chloro-3-hydroxycyclopent-2-en-1,4-dione has been studied. The latter under the action of CH2N2 has been converted to the corresponding enol ether. This methodology has been used for the synthesis of 4-chloro-5-methoxy-2-cinnamylidenecyclopent-4-en-1,3-diones and related compounds starting from the parent dichlorocyclopentenone.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences, 71 prosp. Octyabrya, 450054, Ufa, Russian Federation

    F. A. Gimalova, V. A. Egorov, N. A. Ivanova, A. A. Fatykhov & M. S. Miftakhov

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  1. F. A. Gimalova
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  2. V. A. Egorov
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  3. N. A. Ivanova
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  4. A. A. Fatykhov
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  5. M. S. Miftakhov
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Corresponding author

Correspondence to M. S. Miftakhov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 821-825, April, 2009.

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Gimalova, F.A., Egorov, V.A., Ivanova, N.A. et al. Unusual removal of the ethylene ketal protection from 2,3-dichloro-4,4-ethylenedioxycyclopent-2-en-1-one under alkaline conditions. Simple synthesis of naturally occurring cyclopentenedione analogs. Russ Chem Bull 58, 838–843 (2009). https://doi.org/10.1007/s11172-009-0103-6

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  • DOI: https://doi.org/10.1007/s11172-009-0103-6

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