تفاعل #40659

معادلة التفاعل

LiAlH4

1a

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

Na2SO4

LiAlH4

→

1b

المردود 93.0%

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

المردود 93.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe resulting mixture was warmed gradually
2. 2
   درجة الحرارةto reflux
3. 3
   درجة الحرارةheated
4. 4
   درجة الحرارةat reflux for 5.5 h
5. 5
   ترشيحThe mixture was filtered
6. 6
   غسيلrinsed with EtOAc
7. 7
   غسيلThe organic was washed with H2O, brine
8. 8
   تجفيفdried (MgSO4)
9. 9
   تركيزconcentrated to dryness
10. 10
    أخرىIt was purified by flash chromatography (silica gel, 0-20% EtOAc in hexanes)

الإجراء التجريبي

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).

المصدر