Studies on ketene and its derivatives. LXXXV. Reactions of 4-bromo-3-hydroxybutanoate and its acyl derivatives.
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Acylation of ethyl 4-bromo-3-hydroxybutanoate (I) with acetic anhydride, benzoyl chloride, diketene, and phenyl isocyanate gave rise to ethyl 3-acetoxy-4-bromobutanoate (IIa), ethyl 3-benzoyloxy-4-bromobutanoate (IIb), ethyl 3-acetoacetoxy-4-bromobutanoate (IIc), and ethyl 4-bromo-3-(N-phenylcarbamoyloxy) butanoate (IId), respectively. Reaction of IIa with sodium ethoxide in abs. ethanol gave ethyl 4-hydroxycrotonate (III) and ethyl 4-bromocrotonate (IV). The similar reaction of IIb afforded IV and 4-benzoyloxycrotonate (Vb). Similarly, IIc was converted to III, 4-acetoacetoxycrotonate (Vc), and 3-acetyl-4-ethoxycarbonylmethyltetrahydrofuran-2-one (VI). On the other hand, reaction of IId under the same condition did not give the acyl migrated product such as ethyl 4-N-phenylcarbamoyloxycrotonate (Vd) but afforded ethyl 4-anilinocrotonate (VIII).
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 25 (10), 2692-2696, 1977
公益社団法人 日本薬学会
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- CRID
- 1390001204170495616
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- NII論文ID
- 110003622248
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DyaE1cXltVagsQ%3D%3D
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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
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