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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.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 30 (2), 552-558, 1982
公益社団法人 日本薬学会
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詳細情報
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- CRID
- 1390001204166278016
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- NII論文ID
- 110003634313
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可