Réaction #42520

Équation de réaction

methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

cesium bicarbonate

n-butyl bromide

→

methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

Rendement 67.1%

Solvants

THF

EtOAc

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was heated
2. 2
   Températureat reflux for 48 h
3. 3
   LavageThe organic layer was washed with water, and brine
4. 4
   Séchagedried (magnesium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutrePurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

Mode opératoire

To a stirred solution of methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate (180 mg, 0.94 mmol) and cesium bicarbonate (1.5 g, 4.7 mmol) in THF (2 mL) was added n-butyl bromide (1.0 mL, 9.4 mmol), and the reaction mixture was heated at reflux for 48 h. The reaction mixture was cooled to room temperature, and diluted with EtOAc. The organic layer was washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes) afforded methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (156 mg): ESI MS m/z 248 [M+H]+.

Source