تفاعل #42520

معادلة التفاعل

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

cesium bicarbonate

n-butyl bromide

→

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

المردود 67.1%

المذيبات

THF

EtOAc

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 48 h
3. 3
   غسيلThe organic layer was washed with water, and brine
4. 4
   تجفيفdried (magnesium sulfate)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

الإجراء التجريبي

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]+.

المصدر