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Hydroxymethylation of methyl-substituted pyrrole, thiophene, and furan in the presence of H+ cation exchangers

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

In the reaction of formalin with the 2,5-dimethyl derivatives of pyrrole, thiophene, and furan in the presence of the sulfo cation exchanger Amberlyst 15 electrophilic substitution takes place at various positions of the rings with the formation of 2,5-dimethyl-1-hydroxymethylpyrrole, 1,3-dioxacycloheptano[5,6-c]-2,5-dimethylthiophene (an intermediate in the formation of which is 2,5-dimethyl-3,4-dihydroxymethylthiophene), and 2,5-hexanedione respectively. Bis(5-methyl-2-thienyl)methane was obtained from 2-methylthiophene.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Latvian Academy of Sciences, Riga

    I. G. Iovel', Yu. Sh. Gol'dberg & M. V. Shimanskaya

Authors
  1. I. G. Iovel'
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  2. Yu. Sh. Gol'dberg
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  3. M. V. Shimanskaya
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1640–1643, December, 1991.

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Iovel', I.G., Gol'dberg, Y.S. & Shimanskaya, M.V. Hydroxymethylation of methyl-substituted pyrrole, thiophene, and furan in the presence of H+ cation exchangers. Chem Heterocycl Compd 27, 1316–1318 (1991). https://doi.org/10.1007/BF00515576

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  • DOI: https://doi.org/10.1007/BF00515576

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