Reaktion #40659

Reaktionsgleichung

LiAlH4

1a

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

Na2SO4

LiAlH4

→

1b

Ausbeute 93.0%

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

Ausbeute 93.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was warmed gradually
2. 2
   Temperaturto reflux
3. 3
   Temperaturheated
4. 4
   Temperaturat reflux for 5.5 h
5. 5
   FiltrationThe mixture was filtered
6. 6
   Waschenrinsed with EtOAc
7. 7
   WaschenThe organic was washed with H2O, brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Einengenconcentrated to dryness
10. 10
    SonstigeIt was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

Vorschrift

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).

Quelle