Reaktion #3434

Reaktionsgleichung

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

BBr3 CH2Cl2

→

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

Ausbeute 49.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated 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

A solution of 1.25 g (5 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole and 20 mL of 1M BBr3 /CH2Cl2 in 50 mL of methylene chloride was stirred at room temperature for 5 hours and concentrated 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 577 mg (49% yield) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole, 125°-127° C.

Quelle