تفاعل #654558

معادلة التفاعل

H2O

NaH

4-methoxyindole

benzyl bromide

→

title compound

1-Benzyl-4-methoxyindole

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe layers were separated
2. 2
   استخلاصthe aqueous phase was extracted with EtOAc (2×200 mL)
3. 3
   غسيلThe combined organic layers were washed with H2O (4×500 mL)
4. 4
   تجفيفdried over Na2SO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude residue was purified by flash chromatography (SiO2; hexanes)

الإجراء التجريبي

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);

المصدر