Studies on chrysanthemate derivatives. VI. A stereoselective synthesis of trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid and related compounds.
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概要
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A new method is described for the stereoselective synthesis of <I>trans</I>-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid (<B>2t</B>) <I>via</I> ethyl 3,3-dimethyl-4,6,6,6-tetrachlorohexanoate (<B>3a</B>) as a key intermediate. The key intermediate (<B>3a</B>) was obtained by addition of carbon tetrachloride to ethyl 3,3-dimethyl-4-pentenoate, prepared by condensation of 3-methyl-2-buten-1-ol and triethyl orthoacetate followed by Claisen rearrangement. Treatment of <B>3a</B> with sodium <I>t</I>-pentyloxide in benzene gave ethyl <I>trans</I>-2,2-dimethyl-3-(2,2,2-trichloroethyl)-1-cyclopropanecarboxylate (<B>6t</B>) in good yield. Dehydrochlorination and hydrolysis of <B>6t</B> using potassium hydroxide in ethanol afforded <B>2t</B> in high yield.
- 公益社団法人 日本化学会の論文
著者
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IDE Junya
Central Research Laboratories, Sankyo Co.
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MURAMATSU Shigeki
Central Research Laboratories, Sankyo Co.
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ENDO Rokuro
Central Research Laboratories, Sankyo Co.
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NAKADA Yasuo
Central Research Laboratories, Sankyo Co.
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Yura Yasuo
Central Research Laboratories, Sankyo Co., Ltd.
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Muramatsu Shigeki
Central Research Laboratories, Sankyo Co., Ltd.
関連論文
- Studies on chrysanthemate derivatives. VI. A stereoselective synthesis of trans-3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid and related compounds.
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