Réaction #3458

Équation de réaction

2-Ethyl-4-methoxy-1H-indole

NaH

benzyl bromide

→

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

Rendement 49.0%

Solvants

DMF

water

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 4 hours
2. 2
   Extractionextracted twice with ethyl acetate
3. 3
   LavageThe combined ethyl acetate was washed with brine
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated at reduced pressure
6. 6
   AutreThe residue was chromatographed on silica gel
7. 7
   Lavageeluted with 20% EtOAc/hexane

Mode opératoire

2-Ethyl-4-methoxy-1H-indole (4.2 g, 24 mmol) was dissolved in 30 mL of DMF and 960 mg (24 mmol) of 60% NaH/mineral oil was added. After 1.5 hours, 2.9 mL (24 mmol) of benzyl bromide was added. After 4 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 3.1 g (49% yield) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole.

Source