Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=1.[Cl-].[NH4+]>C(OCC)C.C([Li])CCC>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([OH:21])([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:14]=1
To a solution of 3-bromopyridine (640 mg) in diethyl ether (10 ml), n-butyl lithium (2.5M-hexane solution, 1.80 ml) was added at −74° C. After 15 minutes' stirring at the same temperature, a solution of ethyl 2-(4-chlorophenyl)-2-oxoacetate (960 mg) in diethyl ether (100 ml) was added. The temperature of the system was raised to room temperature over 30 minutes, and to the reaction solution saturated aqueous ammonium chloride solution was added and extracted with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The organic layer was condensed under reduced pressure, and the resulting residue was purified on silica gel column chromatography (hexane/ethyl acetate=3/2) to provide ethyl 2-(4-chlorophenyl)-2-hydroxy-2-(3-pyridinyl)acetate (571 mg) as a yellow oily substance.
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