Title

Synthesis and reactions of 2-hydroxy-4-oxo-4-(2,3,5,6-tetrafluoro-4-methoxyphenyl)-but-2-enoic acid methyl ester

Authors

Authors

E. V. Pimenova; O. P. Krasnych; E. A. Goun;D. H. Miles

Comments

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Abbreviated Journal Title

J. Fluor. Chem.

Keywords

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

Abstract

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 Title

Journal of Fluorine Chemistry

Volume

121

Issue/Number

2

Publication Date

1-1-2003

Document Type

Article

Language

English

First Page

201

Last Page

204

WOS Identifier

WOS:000183215400011

ISSN

0022-1139

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