Reaction #3458

Reaction equation

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

NaH

benzyl bromide

→

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

Yield 49.0%

Solvents

DMF

water

Conditions

Workup

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

Procedure

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