Reaction of 4-Haloacetoacetate with Phenols in the Presence of Aluminum Chloride

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概要

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• Reaction of ethyl 4-bromoacetoacetate (1) with phenol in the presence of aluminum chloride gave ethyl 4-bromo-3-hydroxy-3-(2-hydroxyphenyl) butyrate (3a), which can be regarded as an intermediate of the Pechmann reaction. Similar reaction of ethyl 4-chloroacetoacetate (7) with phenol in the presence of aluminum chloride gave the 4-chloroderivative 8a. Compound 3a was treated with either hydrogen chloride in ethanol or triethylamine followed by treatment with p-toluenesulfonic acid to give 4-bromomethylcoumarin (4a) or ethyl 3-benzo [b] furanacetate (6a), respectively. Similarly, reactions of phenol derivatives 2 with 1 gave the corresponding 3-hydroxy-butyrates 3,which were transformed to the coumarins 4 and the 3-benzo [b] furanacetates 6.

• 社団法人日本薬学会の論文
• 1982-02-25

著者

• 千葉 卓男

  Pharmaceutical Institute, Tohoku University

• 千葉 卓男

  Pharmaceutical Institute Tohoku University

• 加藤 鉄三

  東北大学 薬

• 加藤 鉄三

  Pharmaceutical Institute Tohoku University

• 佐藤 裕利

  Pharmaceutical Institute, Tohoku University

• 木村 仁

  Pharmaceutical Institute, Tohoku University

• 木村 仁

  Pharmaceutical Institute Tohoku University

• 佐藤 裕利

  Pharmaceutical Institute Tohoku University

• 土屋 千鶴子

  Pharmaceutical Institute, Tohoku University

• 土屋 千鶴子

  Pharmaceutical Institute Tohoku University

• 加藤 鉄三

  Pharmaceutical Institute. Tohoku University

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