Réaction #2178442

Équation de réaction

1-[3-(benzyloxy)-6-chloropyridin-2-yl]ethanone

aluminum chloride

trimethylammonium chloride

→

compound

Rendement 86.1%

1-(6-chloro-3-hydroxypyridin-2-yl)ethanone

Rendement 86.1%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 4 hr
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous Rochelle salt solution
3. 3
   workup.ADDITIONwas added to the residue
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   LavageThe extract was washed with saturated brine
6. 6
   Séchagedried over magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane)

Mode opératoire

To a suspension (80 mL) of aluminum chloride (14.3 g) in toluene was added trimethylammonium chloride (4.75 g), and the mixture was stirred under argon atmosphere at room temperature for 1 hr. To the mixture was added a solution (80 mL) of 1-[3-(benzyloxy)-6-chloropyridin-2-yl]ethanone (8.66 g) synthesized above in toluene, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous Rochelle salt solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane) to give the title object compound (4.89 g, 86%) as a pale-yellow solid.

Source