Acetaldehyde → (E)-N-ethylidene-2-methylpropane-2-sulfinamide
Reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH:8](=O)[CH3:9]>ClCCl.[O-]S([O-])(=O)=O.[Cu+2]>[CH:8](=[N:7][S:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])[CH3:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of (S)-(−)-2-methyl-2-propanesulfinamide (1.0 g, 8.25 mmol) and acetaldehyde (2.0 mL, 35.61 mmol) in dichloromethane (20 mL) at ambient temperature under nitrogen atmosphere was added CuSO4 (2.9 g, 18.15 mmol). The mixture was stirred at ambient temperature for 18 h. The reaction was filtered through celite and the filtrate solvent was removed under reduced pressure. N-ethylidene-2-methyl-2-propanesulfinamide was obtained as a clear colorless oil (1.18 g; 1H NMR, 400 MHz, CDCl3, 8.8 ppm (q, 11H), 2.24 ppm (d, 3H), 1.2 ppm (s, 9H)).