Reaktion #426222

Reaktionsgleichung

2-methylquinoline-8-carboxylic acid

chlorotrimethylsilane

→

methyl 2-methylquinoline-8-carboxylate

Ausbeute 33.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   TemperaturAfter cooling
4. 4
   Einengenthe reaction was concentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in water
6. 6
   workup.ADDITIONbasified by dropwise addition of saturated aqueous NaHCO3 solution
7. 7
   ExtraktionThe mixture was extracted with EtOAc
8. 8
   WaschenThe combined organic layers were washed with brine
9. 9
   Sonstigedried
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe residue was purified by flash chromatography on silica gel (3:1 hexane/EtOAc)

Vorschrift

To a stirred solution of 2-methylquinoline-8-carboxylic acid (0.830 g, 4.43 mmol) in MeOH (20 mL) was added dropwise chlorotrimethylsilane (2.41 g, 22.2 mmol). The reaction mixture was heated at reflux overnight. After cooling, the reaction was concentrated under reduced pressure. The residue was dissolved in water and basified by dropwise addition of saturated aqueous NaHCO3 solution. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/EtOAc) to give methyl 2-methylquinoline-8-carboxylate (0.290 g, 33%).

Quelle