Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.O1CCCC1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Mg]>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].C(OCC)C>[CH2:15]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1While stirring a mixture of 150 g of 2-bromo-6-methoxypyridine, 4.3 g of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 500 ml of tetrahydrofuran in an ice bath, Grignard reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethyl ether was added dropwise slowly. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography with (1% ethyl acetate/hexane and 1.5% ethyl acetate/hexane), to give 150 g of the title compound.
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