[CH:1]1(Br)[CH2:3][CH2:2]1.[Mg].[CH:6]1(Br)[CH2:8][CH2:7]1.[Mg].[Cl-:11].[NH4+:12].[CH2:13]1[CH2:17][O:16][CH2:15][CH2:14]1>>[Cl:11][C:8]1[CH:6]=[CH:7][N:12]=[C:1]([CH:15]([CH:14]2[CH2:13][CH2:17]2)[OH:16])[C:3]=1[CH3:2]150 ml of a THF solution of 19.30 g of (4-chloro-3-methylpyridine)-2-carbardehyde (VIII) was dropped to 180 ml of THF solution of magnesium cyclopropyl bromide which was prepared from 14.9 ml of cyclopropyl bromide and 4.53 g of magnesium. The resulting mixture was stirred at a room temperature for 12 hours, and poured into saturated ammonium chloride solution and extracted with chloroform. The resulting organic layer was washed with saturated salt water and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 19.58 g of (4-chloro-3-methyl-2-pyridyl)cyclopropylmethane-1-ol (IX).
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