Ethyl Acetate → 3,5-Dimethylpyridin-1-ium-1-olate

Participants

Reaction Steps

To a solution of 3,5-dimethylpyridine (85 g, 0.8 mol) in CHCl3 (1500 mL) was added m-CPBA (180 g, 0.88 mol) in portions at 0° C. Then the mixture was stirred at room temperature for 18 hr. TLC (petroleum ether:EtOAc=1:1) showed the starting material was consumed almost. After diluting with CH2Cl2 (1200 mL), the solution was washed with Na2S2O3(aq.) (600 mL), NaHCO3(aq.) (600 mL) and brine (600 mL). The resulting material was dried over Na2SO4 and concentrated in vacuo to give crude material which was purified by chromatography on silica gel with EtOAc:CH2Cl2=4:1 to afford 3,5-dimethylpyridine 1-oxide (92 g, 93%) as light yellow solid.

Provenance & Evidence