Application of Organolithium and Related Reagents in Synthesis,Part 29 [1]. A Concise Regiospecific Conversion of Benzoic Acids into 5-(2-Carboxyphenyl)-5-phenylpent-2-enoic Acids |
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Authors: | Adam Bieniek Jan Epsztajn Krystyna K Kulikiewicz |
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Institution: | (1) Department of Organic Chemistry, Institute of Chemistry, University ofód, PL-90-136ód, Poland, PL |
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Abstract: | Summary. A convenient two-step protocol preparation of ortho-alkylated (substituent with the carbomethoxy group at the end of five carbon atoms alkyl chain) aromatic carboxylic acids from benzoic acids anilides is described. Ortho-lithiation of benzanilides and subsequent reaction of the generated bis(N- and C-ortho-)-lithiated anilides with aromatic aldehydes provided 3-arylphthalides. In the next step, these phthalides were converted into 5-(2-carboxyphenyl)-5-phenylpent-2-enoic acids by treatment with 1-methoxy-1-trimethylsilyloxybuta-1,3-diene. |
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Keywords: | , Anilides, Carboxylic acids, Lithiation, Phthalides, Silyl enol ethers, |
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