Benzaldehyde → 2-methyl-N-benzylidene-propane-2-sulfinamide

Participants

Reaction Steps

Benzaldehyde (6 mmol, 1 eq), 2-methyl-propane-2-sulfinic acid amide (1 eq) and tetraethyl orthotitanate (3 eq) are dissolved in anhydrous THF under nitrogen (J. Org. Chem. 2003, 68, 9948-9957). The mixture is stirred at room temperature over night. The mixture is poured in brine and stirred vigorously. The resulting suspension is filtered through Celite and the filter cake is extracted with ethyl acetate. The filtrate is transferred to a separatory funnel, where the aqueous layer is separated and extracted 3× with ethyl acetate. The organic layers are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo. Tert.-butane-sulfinic acid 1-phenyl-methylidene amide is obtained as a clear yellowish oil (90% yield); ES-MS (MH+)=210.2; 1H-NMR (DMSO-d6, 400 MHz): δ [ppm] 8.56 (s, 1H), 7.96-7.93 (m, 2H), 7.63-7.53 (m, 3H), 1.19 (s, 9H).

Provenance & Evidence