Chemistry of α-Haloaldehyde. VI. Reaction of 2-Chloro-2-methylpropanal with Benzoylacetonitrile in the Presence of Potassium Carbonate

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概要

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• The reaction of 2-chloro-2-methylpropanal with benzoylacetonitrile in aqueous K<SUB>2</SUB>CO<SUB>3</SUB> has been studied. When 2-chloro-2-methylpropanal was added to a stirred suspension of benzoylacetonitrile in aqueous K<SUB>2</SUB>CO<SUB>3</SUB>, 2-hydroxy-3,3-dimethyl-4-cyano-5-phenyl-2,3-dihydrofuran (<B>7</B>) was obtained. The oxidation of <B>7</B> with CrO<SUB>3</SUB>gave α,α-dimethyl-β-cyano-γ-phenyl-<I>Δ</I><SUP>β,γ</SUP>-butenolide (<B>8</B>). When benzoylacetonitrile was added to a suspension of 2-chloro-2-methylpropanal in aqueous K<SUB>2</SUB>CO<SUB>3</SUB> stirred beforehand for 60 min, the reaction proceeded in a different manner to give the enol tautomer (<B>9b</B>) of 2,4-dibenzoyl-3-(α-hydroxyisopropyl)glutaronitrile (<B>9a</B>) at room temperature, and 2,2-dimethyl-3-(α-carbaminophenacyl)-4-cyano-5-phenyl-2,3-dihydrofuran (<B>11</B>) at 80–90 °C. The alkaline hydrolysis of the nitrile <B>9</B> conducted at 70 °C also afforded the amide <B>11</B>. The nitrile <B>9</B> eliminated one mol of benzoylacetonitrile on treatment with H<SUB>2</SUB>SO<SUB>4</SUB> to afford 2,2-dimethyl-3-hydroxy-4-cyano-5-phenyl-2,3-dihydrofuran (<B>12</B>). Chromic acid oxidation of <B>12</B> gave 2,2-dimethyl-3-oxo-4-cyano-5-phenyl-2,3-dihydrofuran (<B>14</B>), which can be derived from bullatenone in two steps. Structures of compounds <B>11</B>, <B>12</B>, and <B>14</B>, which all possess 2,2-dimethyl-4-cyano-5-phenyl-2,3-dihydrofuran ring, have been confirmed and well correlated by both chemical transformations and spectral data.

• 公益社団法人 日本化学会の論文

著者

• Tsuboi Sadao

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Sakai Takashi

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Takeda Akira

  Department Of Gastroenterology Osaka General Medical Center

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