Réaction #3433

Équation de réaction

benzyl bromide

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

sodium hydride

hexane

→

4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole

Rendement 84.0%

Solvants

water

DMF

DMF

Conditions de réaction

Traitement

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

Mode opératoire

4-Methoxy-2-methyl-1H-indole (1 g, 6.2 mmol) was added to 248 mg (6.2 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 0.74 mL (6.2 mmol) of benzyl bromide 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 1.3 g (84% yield) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole, melting at 96°-116° C.

Source