The Claisen rearrangement of the lithium enolate of 1-(2-thienyl)alkyl alkanoate and the Birch reduction of the resulting 2-(3-thienyl)alkanoic acid.

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概要

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• It was found that the Claisen rearrangement of the lithium enolate of 1-(2-thienyl)alkyl alkanoate in refluxing THF resulted in the formation of 2-(3-thienyl)alkanoic acid (<B>2</B>). Similarly, when the lithium enolate of 4-(2-thienyl)-4-butanolide was stirred at room temperature in the presence of hexamethylphosphoric triamide, 5,6-dihydro-4<I>H</I>-cyclopenta[<I>b</I>]thiophene-4-carboxylic acid was obtained. Further, it was found that the Birch reduction of <B>2</B> and subsequent alkylation with benzyl bromide gave a regioselective ring-opening product, 4-benzylthio-3-ethyl-3-alkenoic acid, in a good yield. The Birch reduction of 2-thienylacetic acid, followed by alkylation with benzyl bromide, also gave (<I>Z</I>)-3-benzylthio-3-hexenoic acid as the main product.

• 公益社団法人 日本化学会の論文

著者

• Kumamoto Takanobu

  Department Of Chemistry Faculty Of Science Tokai University

• Shirai Kozo

  Department Of Chemistry Faculity Of Science Tokai University

• Abe Hideaki

  Department Of Agricultural Policy Division Of Social Environment Graduate School Of Environment Scie

• Sado Mitsuo

  Department of Chemistry, Faculty of Science, Tokai University

• Inuzuka Nobuki

  Department of Chemistry, Faculty of Science, Tokai University

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