| A Facile Synthesis of Ethyl 2,4-Dimethoxy-6-perfluoroalkyl-benzoates via Acyclic Precursors |
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| 作者姓名： | 曹卫国 施志坚 范纯 孙汝淑 |
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| 作者单位： | [1]DepartmentofChemistry,ShanghaiUniversity,Shanghai200436,China [2]KeyLaboratoryofOrganofluorineChemistry,ShanghaiInstituteofOrganicChemistry,ChineseAcademyofSciences,Shanghai200032,China |
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| 基金项目： | Project supported by the National Natural Science Foundation of China (No. 20172037). |
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| 摘 要： | Introduction Polysubstituted arenes are important intermediates in synthetic medicines and dyestuffs, and the fluorinated analogues are more attractive as a result of their lipo-philicity and the increment of activity.1,2 Therefore, to study the convenient and efficient synthesis of polysub-stituted arenes is valuable in organic synthetic method-ology. We have designed a simple synthesis of fluori-nated polysubstituted arenes through the intramolecular Wittig reaction of a new phosphorous ylid…
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| 关 键 词： | 合成 乙基2 4-二甲氧基-6-全氟烃基-安息香酸盐 分子内Wittig反应 非循环前体 |
A Facile Synthesis of Ethyl 2,4-Dimethoxy-6-perfluoroalkyl-benzoates via Acyclic Precursors |
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| CAO,Wei-Guo SHI,Zhi-Jian FAN,Chun SUN,Ru-Shu.A Facile Synthesis of Ethyl 2,4-Dimethoxy-6-perfluoroalkyl-benzoates via Acyclic Precursors[J].Chinese Journal of Chemistry,2004,22(10):1174-1176. |
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| Authors: | CAO Wei-Guo SHI Zhi-Jian FAN Chun SUN Ru-Shu |
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| Institution: | CAO,Wei-Guo SHI,Zhi-Jian FAN,Chun SUN,Ru-Shu Department of Chemistry,Shanghai University,Shanghai 200436,China b Key Laboratory of Organofluorine Chemistry,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,China |
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| Abstract: | The acyclic precursors, methyl 3-perfluoroalkyl-4-carbethoxy-5-methoxy-6-(triphenylphosphoranylidene)hexa- 2,4-dienoates (4) were obtained via the addition reaction of ethyl 3-methoxy-4-(triphenylphosphoranylidene)but-2- enoate (2) with equally molar methyl 2-perfluoroalkynoates (3). Ethyl 2,4-dimethoxy-6-perfluoroalkylbenzoates (5) were synthesized in high yield via an intramolecular elimination of Ph3PO of 4 by heating in anhydrous benzene in a sealed tube. The structure of these compounds was confirmed by IR, 1H, 13C, 2D C-H cosy NMR and mass spectra and elemental analyses. The possible reaction mechanisms were also proposed. |
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| Keywords: | acyclic precursor intramolecular Wittig reaction fluorinated polysubstituted arene ethyl 2 4-di- methoxy-6-perfluoroalkylbenzoate |
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