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Paper | Regular issue | Vol 75, No. 11, 2008, pp.2703-2711
Published online, 23rd June, 2008
DOI: 10.3987/COM-08-11434
A Facile Synthesis of 2-Difluoromethyl-6-methylpyridine-3,5-dicarboxylates

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

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


α,β-Unsaturated trifluoromethyl ketones 1 react with primary enamines 2 in the presence of phosphorus oxychloride / pyridine adsorbed on silica gel, providing 1,4-dihydro-2-methyl-6-trifluoromethylpyridines 3, which undergo dehydrofluorination by use of DBU/piperazine, giving moderate to high yields of 2-difluoromethyl-6-methylpyridine-3,5-dicarboxylates 4.