Dimethylformamide → Propanenitrile, 2-methyl-2-(methylsulfonyl)-
Reaction equation
[CH3:1][S:2]([CH2:5][C:6]#N)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].I[CH3:15].C[N:17]([CH:19]=O)C>>[CH3:15][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[C:19]#[N:17]Participants
5
Procedure
To a solution of 2-(methylsulfonyl)acetonitrile (60 g, 504 mmol) in DMF (252 mL) at 0° C. was added potassium carbonate (209 g, 1511 mmol) portion-wise, followed by iodomethane (136 mL, 1511 mmol). After 15 minutes, the ice bath was removed and the reaction was stirred at RT for 48 hours. The reaction mixture was filtered through a Celite pad, and the filter cake was rinsed with ethyl acetate and ether. The combined filtrates were concentrated and partitioned between ether and water. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the titled intermediate (58 g, 78% yield) as an off-white solid.