Reaktion #3455

Reaktionsgleichung

4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

BBr3 CH2Cl2

→

4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole

Ausbeute 71.0%

Lösungsmittel

EtOAc hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give a material that
2. 2
   Sonstigewas chromatographed on silica gel (
3. 3
   Wascheneluted with 20% EtOAc/hexane

Vorschrift

By the method used in Example 1, Part D, 1.17 g (3.9 mmol) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole was O-demethylated by treating it with 15.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane then 50% EtOAc/hexane) to give 796 mg (71% yield) of 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.

Quelle