반응 #1459934

반응 방정식

5-chloroindole

sodium hydride

methyl iodide

→

5-chloro-1-methylindole

수율 107.8%

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe resulting mixture was stirred at 0° C. for 30 minutes
3. 3
   추출followed by extraction with ethyl acetate
4. 4
   세척The extract was washed with saturated brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONdistilled under reduced pressure
7. 7
   기타to remove the solvent
8. 8
   기타The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1

실험 절차

In DMF (65 ml) was dissolved 5-chloroindole (5.00 g, 33.0 mmol), followed by the addition of sodium hydride (60% in oil, 1.45 g, 36.3 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred further for 30 minutes at the same temperature, methyl iodide (2.46 ml, 39.6 mmol) was added. The resulting mixture was stirred at 0° C. for 30 minutes. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1, v/v) eluate fractions, 5-chloro-1-methylindole (5.89 g, 100%) was obtained as a yellow oil.

출처