m-Chloroperbenzoic acid → 2-(2,6-Dimethylphenyl)sulfinyl-5-methyl-1,3,4-oxadiazole

Participants

Reaction Steps

To an ice-cooled solution of 2-(2,6-dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole (0.350 g, 0.0016 mol) in CH2Cl2 (10 ml) was added dropwise m-CPBA (0.530 g, 0.002 mol, 65% pure) in CH2Cl2 (5 ml). The ice bath was removed and the reaction mixture was stirred at rt for 2 h and treated with sat. aq. Na2S2O3 (2.5 ml) solution and sat. aq. Na2CO3 (10 ml). The organic layer was separated and then the aqueous layer was extracted with CH2Cl2 (2×25 ml), dried (MgSO4) and the solvent evaporated in vacuo. Chromatography on silica gel using ethyl acetate/hexanes (1/1) as the eluant gave 2-(2,6-dimethylphenyl)sulfinyl-5-methyl-1,3,4-oxadiazole (78) (0.125 g, 23%) as a white solid; mp 79°-80° C.

Provenance & Evidence