반응 #40659

반응 방정식

LiAlH4

1a

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

Na2SO4

LiAlH4

→

1b

수율 93.0%

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

수율 93.0%

용매

THF

반응 조건

후처리

1. 1
   온도The resulting mixture was warmed gradually
2. 2
   온도to reflux
3. 3
   온도heated
4. 4
   온도at reflux for 5.5 h
5. 5
   여과The mixture was filtered
6. 6
   세척rinsed with EtOAc
7. 7
   세척The organic was washed with H2O, brine
8. 8
   건조dried (MgSO4)
9. 9
   농축concentrated to dryness
10. 10
    기타It was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

실험 절차

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).

출처