Реакция #3434

Уравнение реакции

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

BBr3 CH2Cl2

→

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

Выход 49.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated at reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried (MgSO4)
5. 5
   КонцентрированиеAfter concentrating at reduced pressure
6. 6
   Другоеthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Методика

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.

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