반응 #3433

반응 방정식

benzyl bromide

4-Methoxy-2-methyl-1H-indole

sodium hydride

hexane

→

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

수율 84.0%

용매

water

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 18 hours
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The ethyl acetate solution was washed with brine
4. 4
   건조dried (MgSO4)
5. 5
   농축after concentrating at reduced pressure
6. 6
   기타the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

실험 절차

4-Methoxy-2-methyl-1H-indole (1 g, 6.2 mmol) was added to 248 mg (6.2 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 15 mL of DMF and after stirring for 0.5 hour, 0.74 mL (6.2 mmol) of benzyl bromide was added. The mixture was stirred at room temperature for 18 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and after concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.3 g (84% yield) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole, melting at 96°-116° C.

출처