[C:1]([CH:3]1[CH2:7][S:6][CH2:5][C:4]1=[O:8])#[N:2].[H-].[Na+].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:15][CH:14]=1>CN(C)C=O>[C:1]([C:3]1([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:17][CH:18]=2)[C:4](=[O:8])[CH2:5][S:6][CH2:7]1)#[N:2]4-Cyano-3-tetrahydrothiophenone (5.0 g) was dissolved in N,N-dimethylformamide (30 ml), then, sodium hydride (oil, about 60%, 950 mg) was added under ice cooling, and stirred at the same temperature for 30 minutes. Then, to the mixture was added a solution of methyl 2-(4-bromomethylphenyl)propionate (10.1 g) in N,N-dimethylformamide (10.0 ml) under ice cooling, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (5.5 g, 46%).
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