反応 #40659

反応方程式

LiAlH4

1a

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

Na2SO4

LiAlH4

→

1b

収率 93.0%

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

収率 93.0%

溶媒

THF

反応条件

後処理

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
   ろ過The mixture was filtered
6. 6
   洗浄rinsed with EtOAc
7. 7
   洗浄The organic was washed with H2O, brine
8. 8
   乾燥dried (MgSO4)
9. 9
   濃縮concentrated to dryness
10. 10
    その他It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

実験手順

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).

出典