Reaktion #3450

Reaktionsgleichung

4-fluorobenzyl chloride

4-Methoxy-2-methyl-1H-indole

sodium hydride

hexane

→

1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole

Ausbeute 84.0%

Lösungsmittel

water

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 18 hours
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe ethyl acetate solution was washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenafter concentrating at reduced pressure
6. 6
   Sonstigethe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Vorschrift

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride was added. The mixture was stirred at room temperature for 18 hours, diluted with water-and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104°-108° C.

Quelle