Reacción #165102

Ecuación de reacción

sodium hydrogencarbonate

m-chloroperbenzoic acid

sodium hydroxide

4-chloro-2-picoline

→

title compound

Rendimiento 18.0%

(4-Chloro-pyridin-2-yl)-methanol

Rendimiento 18.0%

Disolventes

Water

methanol

Water

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónfollowed by extraction with dichloromethane
2. 2
   OtroThe organic layer was separated
3. 3
   Lavadowashed with water and saturated aqueous sodium chloride
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   workup.ADDITIONAcetic anhydride (20 mL) was added to the residue
7. 7
   Otroobtained
8. 8
   Concentraciónby concentrating the filtrate under a reduced pressure
9. 9
   workup.STIRRINGthis was stirred for 1 hour at 100° C
10. 10
    TemperaturaThe reaction mixture was cooled to room temperature
11. 11
    Concentraciónconcentrated under a reduced pressure
12. 12
    workup.STIRRINGwhich was stirred for 1.5 hours at room temperature
13. 13
    Extracciónwas then extracted with ethyl acetate
14. 14
    OtroThe organic layer was separated
15. 15
    Lavadowashed with water and saturated aqueous sodium chloride
16. 16
    Secadodried over anhydrous magnesium sulfate
17. 17
    Filtraciónfiltered
18. 18
    ConcentraciónThe filtrate was concentrated under a reduced pressure
19. 19
    Otrothe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=6:1)

Procedimiento

To a mixture of 4-chloro-2-picoline (1.0 g, 7.84 mmol) and dichloromethane (20 mL), was added m-chloroperbenzoic acid (3.5 g, 13.2 mmol) on an ice bath, which was stirred for 1.5 hours at room temperature. Water and sodium hydrogencarbonate were added to the reaction, followed by extraction with dichloromethane. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. Acetic anhydride (20 mL) was added to the residue obtained by concentrating the filtrate under a reduced pressure, and this was stirred for 1 hour at 100° C. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. A 5 N aqueous sodium hydroxide solution (1.57 mL, 7.87 mmol) was added to a mixture of the resulting residue and methanol (20 mL) on an ice bath, which was stirred for 1.5 hours at room temperature. Water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=6:1) to obtain the title compound (200 mg, 18%).

Fuente