C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=1.[CH:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>O1CCCC1>[Cl:9][C:10]1[C:15]([CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:27])=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[N:11]=1Lithium diisopropylamide (3.7 mL, 1.8 M tetrahydrofuran solution, manufactured by Tokyo Chemical Industry Co., Ltd.) was added to a solution of 2-chloro-6-(trifluoromethyl)pyridine (1.0 g, manufactured by Matrix Chemical LLC) in tetrahydrofuran (55 mL, manufactured by Kanto Chemical Co., Inc.) at −78° C., and the mixture was stirred for 30 minutes at the same temperature. Then, benzaldehyde (1.17 g, manufactured by Kokusan Chemical Co., Ltd.) was added thereto at −78° C., and the mixture was stirred overnight while gradually raising the temperature to room temperature. Water (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×10 mL), washed with brine (20 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=9:1), to give 1.58 g of the title compound. LC-MS: HPLC retention time 1.68 minutes, m/z 288 (M+H), condition C-1.
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