Reaktion #77732

Reaktionsgleichung

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

BBr3

→

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

Ausbeute 54.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenfollowed by concentration at reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   EinengenAfter concentrating at reduced pressure
6. 6
   Sonstigethe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Vorschrift

3.1 g (11.7 mmol) of 2-ethyl-4-methoxy-1-(phenylmethyl)-1H-indole was O-demethylated by treating it with 48.6 mL of 1M BBr3 in methylene chloride with stirring at room temperature for 5 hours, followed by concentration at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.58 g (54% yield) of 2-ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole, mp, 86-90° C.

Quelle