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Issue 5, 1990
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Syntheses of 3-methylpyrrole via methyl 4-methylpyrrole-2-carboxylate. A thermal oxazolone–pyrone rearrangement

John Cornforth, Sir  and  Du Ming-Hui 

Abstract

3-Ethoxy-2-methylpropenal with hippuric acid and acetic anhydride gave 4-(3-ethoxy-2-methylallyl-idene)-2-phenyloxazol-5(4H)-one. By successive treatment with methanolic potassium hydroxide, acetic–hydrochloric acid, and methanolic sodium methoxide, methyl 4-methylpyrrole-2-carboxylate was formed in high overall yield, and was converted into 3-methylpyrrole by hydrolysis and decarboxylation. The oxazolone with sodium hydroxide in acetone or dioxane gave 4-(3-hydroxy-2-methylallylidene)-2-phenyloxazol-5(4H)-one, isomerized in boiling acetone, or on melting, to 3-benzoylamino-5-methylpyran-2-one. 3-Ethoxy-2-methylpropenal condensed with glycine methyl ester to give an enaminal, cyclized in moderate yield to methyl 4-methylpyrrole-2-carboxylate.

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Article type: Paper
DOI: 10.1039/P19900001459
Citation: J. Chem. Soc., Perkin Trans. 1, 1990,0, 1459-1462
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    Syntheses of 3-methylpyrrole via methyl 4-methylpyrrole-2-carboxylate. A thermal oxazolone–pyrone rearrangement

    J. Cornforth and D. Ming-Hui, J. Chem. Soc., Perkin Trans. 1, 1990, 0, 1459
    DOI: 10.1039/P19900001459

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