반응 #1096191

반응 방정식

2-iodoethylmethylether

sodium hydride

indole

→

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

수율 92.4%

용매

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at rt for 2 h
2. 2
   기타quenched with ice/water
3. 3
   추출extracted with tert-butylmethylether
4. 4
   세척The organics were washed
5. 5
   기타dried
6. 6
   농축concentrated
7. 7
   기타The residue was chromatographed on silica gel

실험 절차

To a slurry of sodium hydride (0.932 g, 23.0 mmol) in DMF (30 mL) was added indole (2.52 g, 21 mmol) portionwise at 10-20° C. over 5 minutes. The reaction mixture was stirred at rt for 1.5 h, and 2-iodoethylmethylether (4.8 g, 26 mmol) in DMF (10 mL) was added over 5 minutes. The mixture was stirred at rt for 2 h, quenched with ice/water, and extracted with tert-butylmethylether. The organics were washed, dried, and concentrated. The residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 1-(2-methoxy-ethyl)-1H-indole (3.40 g) as a yellowish liquid. MS (ISP): m/e 176.4 (M+H)+

출처