I[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH3:11])=[CH:5][CH:4]=1.[C-:12]#[N:13].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CN(C)C=O>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:12]#[N:13])=[CH:4][CH:5]=1)[CH2:10][CH3:11]Under argon condition, 1-(iodomethyl)-4-propylbenzene (73.6 mg, 0.283 mmol) was dissolved in 1 mL of well-dried N,N-dimethylformamide (dry DMF) and then sodium cyanide (NaCN; 27.7 mg, 0.566 mmol) was added and the reaction mixture was stirred for 2 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 3 mL of water and the mixture was extracted with diethyl ether (3 mL×3). The organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure and purified by column chromatography to obtain 41.0 mg (0.257 mmol, 91%) of the desired compound.
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