반응 #164100

반응 방정식

Methyl propargyl ether

4-dimethylamino-4-phenylcyclohexanone

lithium bromide

butyl lithium

hexane

benzyl bromide

→

[4-benzyloxy-4-(3-methoxy-prop-1-ynyl)-1-phenyl-cyclohexyl]-dimethylamine

용매

THF

THF

THF

DMSO

water

반응 조건

후처리

1. 1
   온도cooling
2. 2
   추출extracted with cyclohexane (4×20 mL)
3. 3
   세척The organic phase was washed with 20% ammonium chloride solution
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated to low volume in a vacuum
6. 6
   기타The remaining residue was purified by flash chromatography with CHCl3/MeOH (40:1)

실험 절차

Methyl propargyl ether (0.36 g, 5.2 mmol) dissolved in abs. THF (5 mL) was added in drops to a 2.5 M solution of butyl lithium in hexane (2.1 mL, 5.2 mmol) at −30° C. in argon. A solution of 4-dimethylamino-4-phenylcyclohexanone (1.08 g, 5.0 mmol) in abs. THF (5 mL) and lithium bromide (0.22 g, 2.5 mmol) dissolved in abs. THF (2.0 mL) was then added at −30° C. The reaction mixture was heated to −5° C., mixed in drops with a solution of benzyl bromide (1.28 g, 7.5 mmol) in abs. DMSO (10 mL) and stirred 2 h at 50° C. For work up of the reaction mixture water (10 mL) was added with ice bath cooling and extracted with cyclohexane (4×20 mL). The organic phase was washed with 20% ammonium chloride solution, dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by flash chromatography with CHCl3/MeOH (40:1).

출처