Reacción #2439921

Ecuación de reacción

2-phenyl-6-methyl-pyridine

mCPBA

NaHCO3

Na2S2O3

→

2-phenyl-6-methyl-pyridine-N-oxide

Disolventes

chloroform

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.STIRRINGAfter stirring for 1.5 hr
3. 3
   Otroto remove the excess of mCPBA
4. 4
   OtroThe organic layer was dried on MgSO4
5. 5
   OtroRemoval of the drying agent
6. 6
   Filtraciónby filtration and solvent
7. 7
   Otroby evaporation in vacuo
8. 8
   Otroyielded an oil which
9. 9
   Otrocrystallized

Procedimiento

While stirring at room temperature, 4.8 g *28.5 mmol) of 2-phenyl-6-methyl-pyridine were dissolved in 50 ml of chloroform after which a solution of 7.8 g of 75% mCPBA (33.9 mmol) in 75 ml of chloroform were added dropwise. The reaction mixture showed only a slight rise in temperature. After stirring for 1.5 hr, the reaction mixture was shaken twice with 5% aqueous NaHCO3 solution and twice with an aqueous solution of Na2S2O3 to remove the excess of mCPBA, after which the reaction mixture proved to be negative on wet Kl/starch paper, The organic layer was dried on MgSO4. Removal of the drying agent by filtration and solvent by evaporation in vacuo yielded an oil which crystallized upon scratching to give 5.5 g (105%) of crude of 2-phenyl-6-methyl-pyridine-N-oxide, which was employed in the next step without further purification.

Fuente