تفاعل #77732

معادلة التفاعل

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

BBr3

→

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

المردود 54.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   تركيزfollowed by concentration at reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   تركيزAfter concentrating at reduced pressure
6. 6
   أخرىthe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

الإجراء التجريبي

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.

المصدر