Synthesis And Reactions Of 2-Hydroxy-4-Oxo-4-(2,3,5,6-Tetrafluoro-4- Methoxyphenyl)-But-2-Enoic Acid Methyl Ester
2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester; 3-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)-propene-1,3-dione; 5-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)-furan-2,3- dione
2-Hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester (1) was synthesized by the reaction of pentafluoroacetophenone with dimethyl oxalate in the presence of sodium methylate. Subsequently, reactions of compound 1 with aniline, o-phenylenediamine, and o-aminophenol were investigated. In addition, the thermal cyclization of ester 1 was studied and led to the formation of 5,6,8-trifluoro-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid methyl ester (6) due to nucleophilic substitution of the 3-fluoro group. Hydrolysis of compound 1 and subsequent cyclization by treatment with SOCl2 gave 5-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-furan-2, 3-dione (3). Thermal decarbonylation of compound 3 under mild conditions resulted in the formation of 3-(2,3,5,6-tetrafluoro-4-methoxyphenyl)- propene-1,3-dione (4) which dimerized to pyranone 5. © 2003 Elsevier Science B.V. All rights reserved.
Journal of Fluorine Chemistry
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Pimenova, Elena V.; Krasnych, Olga P.; and Goun, Elena A., "Synthesis And Reactions Of 2-Hydroxy-4-Oxo-4-(2,3,5,6-Tetrafluoro-4- Methoxyphenyl)-But-2-Enoic Acid Methyl Ester" (2003). Scopus Export 2000s. 1733.