Reaktion #6651

Reaktionsgleichung

lithium aluminum hydride

4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline

Compound 93

4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline

→

title compound

4,4-Dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline

Lösungsmittel

THF

THF

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux under nitrogen
2. 2
   TemperaturThe mixture was heated
3. 3
   Temperaturat reflux for 2 h
4. 4
   SonstigeThe reaction mixture was then quenched by the slow addition of 25 ml of water
5. 5
   ExtraktionThe mixture was extracted with 2×25 ml of ether
6. 6
   Waschenwashed successively with 25 ml each of water and saturated NaCl solution
7. 7
   Trocknendried (MgSO4)
8. 8
   SonstigeThe solvent was removed in vacuo
9. 9
   Sonstigethe residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes)

Vorschrift

To 23.5 ml of 1.0 M (23.5 mmol) lithium aluminum hydride in THF, heated to reflux under nitrogen, was added to solution of 4.95 g (19.48 mmol) of 4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 93) in 50 ml of dry THF and 100 ml of dry ether via a double-ended needle. The mixture was heated at reflux for 2 h and then cooled to room temperature. The reaction mixture was then quenched by the slow addition of 25 ml of water followed by 50 ml of 5% NaOH solution. The mixture was extracted with 2×25 ml of ether, the organic extracts were combined and washed successively with 25 ml each of water and saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes) to give the title compound as a brown oil. PMR (CDCl3): δ 1.27 (6H, s), 1.67-1.74 (2H, m), 3.23-3.32 (2H, m), 3.90 (1H, broad s), 6.33 (1H, d, J~8.4 Hz), 7.10 (1H, dd, J~8.4 Hz, 2.3 Hz), 7.25 (1H, d, J~2.3 Hz).

Quelle