N. Zanatta, L. S. Rosa, E. Loro
2001
Citations
0
Influential Citations
17
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract The synthesis of a series of novel trifluoromethylated β-acetal- gem -diols, 4-alkoxy-4-ethoxy-1,1,1-trifluoro-butane-2,2-diols ( 4a = methoxy , 4b = ethoxy , 4c = allyloxy , 4d = ynyloxy ) and 1-(2-alkoxytetrahydro-furan-3-yl)-2,2,2-trifluoro-ethane-1,1-diols ( 6a = methoxy , 6b = ethoxy , 6c = allyloxy , 6d = ynyloxy ) from the reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one ( 1 ) and 1-(4,5-dihydro-furan-3-yl)-2,2,2-trifluoro-ethanone ( 2 ) with sodium azide in hydro-alcoholic medium, is presented. From these reactions, a small amount (ca. of 20%) of the parent trifluoromethylated β-acetal-ketones, 4-alkoxy-4-ethoxy-1,1,1-trifluoro-butan-2-ones ( 3a – d ) and 2,2,2-trifluoro-1-(2-alkoxy-tetrahydro-furan-3-yl)-ethanones ( 5a – d ) were also obtained. The synthetic potential of the trifluoromethylated β-acetal-diols was demonstrated by its application to the synthesis of 3-ethoxy-5-hydroxy-5-trifluoromethyl-pyrrolidin-2-one ( 7 ).