反应详情

To an NaH slurry (0.15 g, 0.0037 mol, 60% in oil) in dry DMF (5 ml) under a N2 atmosphere was added 2,6-dimethylthiophenol (0.50 ml, 0.00374 mol). The mixture was stirred for 10 min at rt and cooled to 0° C. To the cooled solution was added dropwise via syringe a solution of 5-methyl-2-sulfinylmethyl-1,3,4-oxadiazole (77) (0.5 g, 0.0034 mol) in dry DMF (1.5 ml). The mixture was stirred for 1 h, water was added (15 ml) and the aqueous layer extracted with Et2O (4×20 ml). The combined extracts were washed with water (2×25 ml), saturated NaCl solution (1×25 ml), dried (MgSO4) and solvent removed in vacuo. Chromatography on silica gel using 1/2 ethyl acetate/hexanes gave 2-(2,6-dimethylphenyl)thio-5-methyl-1,3,4-oxadiazole (24) as a white solid (0.372 g, 46%, mp 53°-54° C.).

1. temperaturecooled to 0° C
2. stirringThe mixture was stirred for 1 h
3. extractionthe aqueous layer extracted with Et2O (4×20 ml)
4. washThe combined extracts were washed with water (2×25 ml), saturated NaCl solution (1×25 ml)
5. dry with materialdried (MgSO4) and solvent
6. customremoved in vacuo