Reaktion #3458

Reaktionsgleichung

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

NaH

benzyl bromide

→

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

Ausbeute 49.0%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 4 hours
2. 2
   Extraktionextracted twice with ethyl acetate
3. 3
   WaschenThe combined ethyl acetate was washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated at reduced pressure
6. 6
   SonstigeThe residue was chromatographed on silica gel
7. 7
   Wascheneluted with 20% EtOAc/hexane

Vorschrift

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.

Quelle