Reaktion #485038

Reaktionsgleichung

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

NaH

benzyl bromide

→

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

Ausbeute 49.0%

Lösungsmittel

DMF

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

2-Ethyl-4-methoxy-1H-indole (4.2 g, 24 mmol) is dissolved in 30 mL of DMF and 960 mg (24 mmol) of 60% NaH/mineral oil is added. After 1.5 hours, 2.9 mL (24 mmol) of benzyl bromide is added. After 4 hours, the mixture is diluted with water extracting twice with ethyl acetate. The combined ethyl acetate is washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue is 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