반응 #42520

반응 방정식

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

cesium bicarbonate

n-butyl bromide

→

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

수율 67.1%

용매

THF

EtOAc

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도at reflux for 48 h
3. 3
   세척The organic layer was washed with water, and brine
4. 4
   건조dried (magnesium sulfate)
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

실험 절차

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]+.

출처