Reacción #40659

Ecuación de reacción

LiAlH4

1a

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

Na2SO4

LiAlH4

→

1b

Rendimiento 93.0%

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

Rendimiento 93.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was warmed gradually
2. 2
   Temperaturato reflux
3. 3
   Temperaturaheated
4. 4
   Temperaturaat reflux for 5.5 h
5. 5
   FiltraciónThe mixture was filtered
6. 6
   Lavadorinsed with EtOAc
7. 7
   LavadoThe organic was washed with H2O, brine
8. 8
   Secadodried (MgSO4)
9. 9
   Concentraciónconcentrated to dryness
10. 10
    OtroIt was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

Procedimiento

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).

Fuente