Reacción #164101

Ecuación de reacción

Methyl propargyl ether

4-dimethylamino-4-phenylcyclohexanone

lithium bromide

butyl lithium

hexane

ethyl iodide

→

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

Disolventes

THF

THF

THF

DMSO

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Extracciónextracted with cyclohexane (4×50 mL)
3. 3
   LavadoThe organic phase was washed with 20% ammonium chloride solution
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated to low volume in a vacuum
6. 6
   OtroThe remaining residue was purified by flash chromatography with CHCl3/MeOH (20:1)

Procedimiento

Methyl propargyl ether (1.47 g, 21.0 mmol) dissolved in abs. THF (15 mL) was added in drops to a 2.5 M solution of butyl lithium in hexane (8.4 mL, 21.0 mmol) at −30° C. in argon. A solution of 4-dimethylamino-4-phenylcyclohexanone (4.34 g, 20.0 mmol) in abs. THF (20 mL) and lithium bromide (0.87 g, 10 mmol) dissolved in abs. THF (2.5 mL) was then added at −30° C. The reaction mixture was heated to −5° C., mixed in drops with a solution of ethyl iodide (4.68 g, 30 mmol) in abs. DMSO (30 mL) and stirred for 2 h at 50° C. For work up of the reaction mixture water (30 mL) was added with ice bath cooling and extracted with cyclohexane (4×50 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 (20:1).

Fuente