To a solution of 4.0 g (0.0145 mol) of 3-hydroxy-5-(4-mercaptophenyl)-2-propionyl-cyclohex-2-en-1-one in 50 mL of acetonitrile was added 3.90 g (0.0212 mol) of 2,3-difluoro-5-(trifluoromethyl)pyridine and 4.50 g (0.0326 mol) of powdered potassium carbonate. The mixture was stirred one hour at ambient temperature and then heated at reflux for 1.5 hours and cooled to room temperature. The reaction mixture was diluted with 150 mL of water and 150 mL of methylene chloride. The organic layer was separated, washed twice with 150 mL portions of water and dried over Na2SO4. The solvent was removed in vacuo leaving 5.7 g of the crude product which was purified by column chromatography using methylene chloride as the eluent. Recrystallization of the crude from ethanol gave the above named product in a yield of 2.25 g (35 percent of theoretical). The product melted at 152°-154° C.; 1H NMR (CDCl3): δ 1.10 (t, 3H, CH3CH2 --), 2.55-3.65 (m, 7H, ring protons and CH3CH2 --), 7.15-8.50 (m, 6H, ArH), 18.2 (s, 1H, OH).
