Preparation of methyl 2-arylpropanoates by the reaction of 2-hydroxypropiophenone dimethyl acetals with sulfuryl chloride in the presence of an amide or a weak base.

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概要

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• Treatment of 2-hydroxypropiophenone dimethyl acetals [<I>p</I>-RC<SUB>6</SUB>H<SUB>4</SUB>C(OMe)<SUB>2</SUB>CH(OH)Me] (<B>1</B>; R=H, <I>i</I>-Bu, OMe, Ph, Br) with sulfuryl chloride in the presence of an amide or a weak base affords methyl 2-arylpropanoates (<B>2</B>) in good to excellent yields via 1,2-aryl migration of <B>1</B>. The hydrolysis of <B>2</B> leads to the corresponding acids, some of which are pharmaceutically important compounds having nonsteroidal anti-inflammatory and analgesic activities. The aryl migration proceeds stereospecifically with complete inversion of configuration at the β-carbon atom.

• 公益社団法人 日本化学会の論文

著者

• Nakao Kenji

  Sakai Research Laboratories, Sakai Plant, Kyowa Hakko Kogyo Co. Ltd.

• Tamaki Kentaro

  Sakai Research Laboratories, Sakai Plant, Kyowa Hakko Kogyo Co. Ltd.

• Hattori Kaneaki

  Sakai Research Laboratories, Sakai Plant, Kyowa Hakko Kogyo Co. Ltd.

• Yamauchi Takayoshi

  Sakai Research Laboratories, Sakai Plant, Kyowa Hakko Kogyo Co. Ltd.

関連論文

• Preparation of methyl 2-arylpropanoates by the reaction of 2-hydroxypropiophenone dimethyl acetals with sulfuryl chloride in the presence of an amide or a weak base.

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