Reaktion #595101

Reaktionsgleichung

Water

sodium hydride

3-bromo-2-phenyl-1H-indole

2-chloroethyl ethyl ether

→

title compound

Ausbeute 76.0%

3-bromo-1-(2-ethoxyethyl)-2-phenyl-1H-indole

Ausbeute 76.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUnder ice-cooling
2. 2
   workup.STIRRINGthe mixture was stirred at 70° C. for 3 hr
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe extract was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe obtained residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane)

Vorschrift

Under ice-cooling, sodium hydride (60% in oil, 0.48 g, 12.0 mmol) was added to a solution of 3-bromo-2-phenyl-1H-indole (2.72 g, 10.0 mmol) in N,N-dimethylformamide (10 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 30 min. To the reaction mixture was added 2-chloroethyl ethyl ether (1.65 mL, 15.0 mmol), and the mixture was stirred at 70° C. for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-25% ethyl acetate/hexane) to give the title compound (2.60 g, yield 76%) as a red oil.

Quelle