Реакция #42520

Уравнение реакции

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

cesium bicarbonate

n-butyl bromide

→

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

Выход 67.1%

Растворители

THF

EtOAc

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   Температураat reflux for 48 h
3. 3
   ПромывкаThe organic layer was washed with water, and brine
4. 4
   Сушкаdried (magnesium sulfate)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

Методика

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]+.

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