REACTION OF ETHYL 4,4,4-TRIFLUOROACETOACETATE ENOLATE WITH 3-BROMO-1,1,1-TRIFLUOROACETONE - SYNTHESIS OF 2,4-BIS(TRIFLUOROMETHYL)FURAN

Authors
SMITH JO MANDAL BK FILLER R BEERY JW
Citation
Jo. Smith et al., REACTION OF ETHYL 4,4,4-TRIFLUOROACETOACETATE ENOLATE WITH 3-BROMO-1,1,1-TRIFLUOROACETONE - SYNTHESIS OF 2,4-BIS(TRIFLUOROMETHYL)FURAN, Journal of fluorine chemistry, 81(2), 1997, pp. 123-128
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Journal of fluorine chemistry → ACNP
ISSN journal
00221139
Volume
81
Issue
2
Year of publication
1997
Pages
123 - 128
Database
ISI
SICI code
0022-1139(1997)81:2<123:ROE4EW>2.0.ZU;2-1
Abstract
The potassium enolate of ethyl 4,4,4-trifluoroacetoacetate 1 reacts wi th 3-bromo-1,1,1-trifluoroacetone 2 in DMSO solution to yield three pr oducts. Ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro 3 is generated via C-acylation. The hydrated trifluoromethyl ketone 4 is formed by O -alkylation and 4 reacts further with 2 to give the di-O-alkylated ket one hydrate 5. Compound 3 undergoes dehydration to the furan derivativ e 6 on reaction with Ac2O-ZnCl2.