[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH:7]=[C:8]([C:10]#N)[O:9][C:5]=2[CH:4]=1.[O:14]1CCCC1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[NH4+]>O1CCCC1>[CH:19]1([C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=3[CH:7]=2)=[O:14])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1To a solution (20 mL) of 6-methoxy-1-benzofuran-2-carbonitrile (1.00 g) synthesized above in tetrahydrofuran was added 1.0M cyclohexylmagnesium bromide tetrahydrofuran solution (11.5 mL), and the mixture was stirred at 50° C. overnight, and stirred with heating under reflux for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (584 mg, 39%) as a yellow solid.
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