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Synthesis 2000; 2000(11): 1603-1607
DOI: 10.1055/s-2000-7610
DOI: 10.1055/s-2000-7610
paper
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Application of Organolithium and Related Reagents in Synthesis, Part 24. Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Conversion of Benzoic Acids into 2-(1-Aryl-2-methoxycarbonylethyl)benzoic Acids
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Publication History
Publication Date:
31 December 2000 (online)
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The synthesis of the 3-arylphthalides 3 via metallation (BuLi) of the benzanilides 1 and subsequent reaction of the generated bis-lithiated anilides 2 with aromatic aldehydes is described. Conversion of 3 into the corresponding 2-(1-aryl-2-methoxycarbonylethyl)benzoic acids 4 by treatment with 1-methoxy-1-trimethylosiloxyethene in the presence of titanium tetrachloride, as a way of regiospecific transformation of benzoic acids, is also described.
lithiation - anilides - phthalides - silyl enol ethers - benzoic acids