Reaktion #2178431

Reaktionsgleichung

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

aluminum chloride

trimethylammonium chloride

→

compound

Ausbeute 83.0%

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

Ausbeute 83.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 3 hr
3. 3
   EinengenThe reaction mixture was concentrated under reduced pressure, saturated aqueous Rochelle salt solution
4. 4
   workup.ADDITIONwas added to the residue
5. 5
   Extraktionthe mixture was extracted with ethyl acetate
6. 6
   WaschenThe extract was washed with saturated brine
7. 7
   Trocknendried over magnesium sulfate
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   SonstigeThe residue was purified by silica gel column chromatography (0-5% ethyl acetate/hexane)

Vorschrift

To a suspension (30 mL) of aluminum chloride (3.96 g) in toluene was added trimethylammonium chloride (1.32 g), and the mixture was stirred under argon atmosphere at room temperature for 1 hr. A solution (30 mL) of 1-[3-(benzyloxy)-6-bromopyridin-2-yl]ethanone (2.81 g) synthesized above in toluene was added to the mixture, and the mixture was stirred at room temperature for 3 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 (1.64 g, 83%) as a yellow solid.

Quelle