반응 #79740

반응 방정식

H2O

NaH

4-methoxyindole

benzyl bromide

→

title compound

1-Benzyl-4-methoxyindole

용매

DMF

반응 조건

후처리

1. 1
   기타The layers were separated
2. 2
   추출the aqueous phase was extracted with EtOAc (2×200 mL)
3. 3
   세척The combined organic layers were washed with H2O (4×500 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude residue was purified by flash chromatography (SiO2; hexanes)

실험 절차

NaH (7.7 g, 191.7 mmol) was added portionwise to a 0° C. solution of 4-methoxyindole (21.7 g, 147 mmol) in 750 mL of anhydrous DMF. After 15 min, the slurry was treated with benzyl bromide (17.5 mL, 147 mmol). The reaction mixture was allowed to warm to ambient temperature and stir overnight. The reaction mixture was poured into 1 L of H2O. The layers were separated, and the aqueous phase was extracted with EtOAc (2×200 mL). The combined organic layers were washed with H2O (4×500 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2; hexanes) to give 32.9 g (138.6 mmol; 94%) of the title compound as a white solid. Electrospray MS 238 (M+1);

출처