CON(C)[C:4](=[O:21])[CH:5]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][N:14]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH:23]([Mg]Br)=[CH2:24].Cl>O1CCCC1>[CH3:20][S:19][C:16]1[CH:17]=[CH:18][C:13]([CH:5]([CH2:6][CH:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[C:4](=[O:21])[CH:23]=[CH2:24])=[N:14][CH:15]=1A solution of N-methoxy-N-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (404 mg) in tetrahydrofuran (5 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 5.0 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 2 hr, and poured into 1M hydrochloric acid, and the mixture was stirred for 30 min. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (168 mg, yield 46%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).
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