Reacción #79740

Ecuación de reacción

H2O

NaH

4-methoxyindole

benzyl bromide

→

title compound

1-Benzyl-4-methoxyindole

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe layers were separated
2. 2
   Extracciónthe aqueous phase was extracted with EtOAc (2×200 mL)
3. 3
   LavadoThe combined organic layers were washed with H2O (4×500 mL)
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   OtroThe crude residue was purified by flash chromatography (SiO2; hexanes)

Procedimiento

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);

Fuente