反応 #3450

反応方程式

4-fluorobenzyl chloride

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

sodium hydride

hexane

→

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

収率 84.0%

溶媒

water

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 18 hours
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The ethyl acetate solution was washed with brine
4. 4
   乾燥dried (MgSO4)
5. 5
   濃縮after concentrating at reduced pressure
6. 6
   その他the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

実験手順

4-Methoxy-2-methyl-1H-indole (805 mg, 5 mmol) was added to a mixture of 200 mg (5 mmol) of 60% sodium hydride/mineral oil (washed with hexane before adding DMF) in 10 mL of DMF and after stirring for 0.5 hours, 0.6 mL (5 mmol) of 4-fluorobenzyl chloride 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 1.1 g (84% yield) of 1-[(4-fluorophenyl)methyl]-4-methoxy-2-methyl-1H-indole, melting at 104°-108° C.

出典