The Regioselective Side-Chain Lithiation of 2-Methyl-3-thiophenecarboxylic Acid

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  • Su Hui-Wen
    Department of Chemistry, Faculty of Science, Tokai University
  • Kazuo Hirose
    Department of Chemistry, Faculty of Science, Tokai University
  • Kozo Shirai
    Department of Chemistry, Faculty of Science, Tokai University
  • Takanobu Kumamoto
    Department of Chemistry, Faculty of Science, Tokai University

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<jats:title>Abstract</jats:title> <jats:p>It was found that the dilithium salt (5), which was lithiated at the side-chain of 2-methyl-3-thiophenecarboxylic acid (4), was produced regioselectively by the reaction of 4 with lithium diisopropylamide (LDA). The reactions of 5 with alkyl halides resulted in the formation of 2-alkyl-3-thiophenecarboxylic acids (7). Further, δ-lactone derivatives (11) were obtained by the cyclization of the adducts (10) which were produced from 5 with aldehydes and ketones.</jats:p>

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