The Birch Reduction of Heterocyclic Carboxylic Acids. I. The Birch Reduction of 3-Furoic Acid

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概要

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• The reduction of 3-furoic acid with sodium and 2-propanol in liquid ammonia gave 2,3-dihydro-3-furoic acid, which was isolated as a methyl ester (<B>1</B>) in 85% yield. The acid-catalyzed addition of methanol, ethanol, or 2-propanol to the ester <B>1</B> yielded 5-alkoxytetrahydro-3-furoate ester, <B>2</B>, <B>3</B>, or <B>4</B>, respectively, in a quantitative yield. When methanol or ethanol was used as a proton source in the reduction, work-up of the reaction mixture gave 5-alkoxytetrahydro-3-furoic acid, which was isolated as the methyl ester, <B>2</B> or <B>3</B>, in 87 or 92% yield, respectively. A mechanism for the Birch reduction of aromatic carboxylic acids is proposed.

• 公益社団法人 日本化学会の論文

著者

• Miwa Toshio

  Faculty of Science, Osaka City University

• Kinoshita Takamasa

  Faculty of Science, Osaka City University

• Miyano Kouichi

  Faculty of Science, Osaka City University

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