CN(C)CCN(C)C.C([Li])CCC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([SH:22])[CH:19]=[CH:20][CH:21]=1.CON(C)[C:26](=[O:35])[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C1CCCCC1>[SH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH3:14])[C:17]=1[C:26](=[O:35])[CH:27]=[CH:28][CH:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH2:34]1To a solution of N,N,N′,N′-tetramethylethylenediamine (4.31 mL) in cyclohexane (50 ml) were added n-butyl lithium (2.46 mol/L n-hexane solution 12.2 mL) and 3-methoxythiophenol (2 g) successively under ice-cooling. The reaction mixture was stirred at room temperature overnight. To the reaction mixture was added N-methoxy-N-methyl-3-phenylpropionamide (2.76 g) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=10/1-5/1) to give the title compound (1.2 g).
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