Synthesis and reactions of 2-hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester
Abbreviated Journal Title
J. Fluor. Chem.
hydroxy-4-oxo-4-(2, 3, 5, 6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid; methyl ester; 5-(2, 3, 5, 6-tetrafluoro-4-methoxyphenyl)-furan-2, 3-dione; 3-(2, 3, 5, 6-tetrafluoro-4-methoxyphenyl)-propane-1, 3-dione; 5-MEMBERED 2, 3-DIOXOHETEROCYCLES; Chemistry, Inorganic & Nuclear; Chemistry, Organic
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 penta-fluoroacetophenone,with dimethyl oxalate in the presence of sodium methylate. Subsequently, reactions of compound I with aniline, o-phenylenediamine. and o-aminophenol were investigated. In addition, the thermal cyclization of ester I 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 I 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-methoxvphenyl)-propene-1, 3-dione (4) which dimerized to pyranone 5. (C) 2003 Elsevier Science B.V. All rights reserved.
Journal of Fluorine Chemistry
"Synthesis and reactions of 2-hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester" (2003). Faculty Bibliography 2000s. 3965.