Sodium Hydroxide → (6-Chloropyridin-2-yl)methanol

Temperatur

40 °C

To a mixture of 2-chloro-6-methylpyridine (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 40° C. Water and sodium hydrogencarbonate were added to the reaction mixture, which was then extracted with dichloromethane. 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. Acetic anhydride (20 mL) was added to the resulting residue and 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 (4 mL, 20.1 mmol) was added to a mixture of the resulting residue and methanol (20 mL) on an ice bath, which was stirred for 30 minutes. Water was added to this 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=3:1) to obtain the title compound (200.0 mg, 18%).

1. extractionwas then extracted with dichloromethane
2. customThe organic layer was separated
3. washwashed with water and saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under a reduced pressure
7. additionAcetic anhydride (20 mL) was added to the resulting residue
8. stirringstirred for 1 hour at 100° C
9. temperatureThe reaction mixture was cooled to room temperature
10. concentrationconcentrated under a reduced pressure
11. stirringwhich was stirred for 30 minutes
12. extractionwas then extracted with ethyl acetate
13. customThe organic layer was separated
14. washwashed with water and saturated aqueous sodium chloride
15. dry with materialdried over anhydrous magnesium sulfate
16. filtrationfiltered
17. concentrationThe filtrate was concentrated under a reduced pressure
18. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=3:1)

ORD-Eintrag

ord-1a3c3579a2d04bccb7de7ad11a293dc1

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841327B2