反应 #40659

反应方程式

LiAlH4

1a

4,4-Dimethyl-3,4-dihydro-1H-quinolin-2-one

Na2SO4

LiAlH4

→

1b

收率 93.0%

4,4-dimethyl-1,2,3,4-tetrahydroquinoline

收率 93.0%

溶剂

THF

反应条件

后处理

1. 1
   温度The resulting mixture was warmed gradually
2. 2
   温度to reflux
3. 3
   温度heated
4. 4
   温度at reflux for 5.5 h
5. 5
   过滤The mixture was filtered
6. 6
   洗涤rinsed with EtOAc
7. 7
   洗涤The organic was washed with H2O, brine
8. 8
   干燥dried (MgSO4)
9. 9
   浓缩concentrated to dryness
10. 10
    其他It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

实验过程

To a stirred solution of LiAlH4 (1.0 M in THF, 35 mL, 35 mmol), was added a solution of 1a. (2.17 g, 12.4 mmol) in THF (10 mL) for 5 min at 0° C. under nitrogen. The resulting mixture was warmed gradually to reflux, and heated at reflux for 5.5 h. To the cooled mixture with stirring, was added sat'd Na2SO4 dropwise till the complete decomposition of LiAlH4. The mixture was filtered, and rinsed with EtOAc. The organic was washed with H2O, brine, dried (MgSO4), and concentrated to dryness. It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes) to give pure 1b (1.86 g, yield: 93%). LC-MS ESI 162 (M+H).

来源