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Paper | Regular issue | Vol 68, No. 10, 2006, pp.2087-2096
Published online, 29th August, 2006
DOI: 10.3987/COM-06-10827
An Efficient Synthesis of 1,4-Dihydro-6-trifluoromethylpyridines: A Facile and Useful Method for Dehydration of α-Trifluoromethyl Alcohols by Use of Phosphorous Oxychloride/Pyridine Adsorbed on Silica Gel

Isamu Katsuyama,* Kazumasa Funabiki, Masaki Matsui, Hiroshige Muramatsu, and Katsuyoshi Shibata

*Hitec Co., Ltd, OAP 25F, 1-8-30 Temmabashi, Kita-ku, Osaka-shi, Osaka 530-6025, Japan


The treatment of α-alkoxycarbonyl-α,β-unsaturated trifluoromethyl ketones (1) with β-aminocrotonates (2) affords 2-hydroxy-6-methyl-2- trifluoromethyl-1,2,3,4-tetrahydropyridines (3), which undergo facile dehydration by use of phosphorus oxychloride / pyridine adsorbed on silica gel, giving good to high yields of 1,4-dihydro-2-methyl-6-trifluoromethylpyridines (4).