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Synthesis 1999; 1999(5): 765-768
DOI: 10.1055/s-1999-3457
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Reactions of 1,1,1-Trifluoro[chloro]-4-ethoxybut-3-en-2-ones with 1,3-Dicarbonyl Compounds: Synthesis of 5-Acetyl[carboxyethyl]-1,1,1-trifluoro[chloro]hept-3-ene-2,6-diones and their Cyclic Derivatives Phenol, Pyridines, and Azetone

Nilo Zanatta* , Rosemario Barichello, Helio G. Bonacorso, Marcos A. P. Martins
  • *Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil; Fax +55(0 55)2 20 80 31; E-mail: zanatta@base.ufsm.br
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Publication Date:
31 December 1999 (online)

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The synthesis of 5-acetyl[carboxyethyl] 1,1,1-trifluoro[chloro]hept-3-ene-2,6-diones (3a,b, 4a,b) and their cyclic derivatives 1-[2-hydroxy-4-(trifluoromethyl)phenyl]ethanone (5a), 1-[2-hydroxy-6-(trichloro[fluoro]methyl)pyridin-3-yl]ethanone (6c, 7c), and 3-acetylazet-2(1H)-one (8), obtained from the reactions of 1,1,1-trifluoro[chloro]-4-ethoxybut-3-en-2-one (1, 2), with 1,3-dicarbonyl compounds such as acetylacetone (a), ethyl acetoacetate (b), and acetoacetamide (c) and sodium hydride in anhydrous THF, is reported.

1,1,1-Trifluoro[chloro]-4-ethoxybut-3-en-2-ones - dicarbonyl compounds - pyridines - phenols - azetones