Reacción #337380

Ecuación de reacción

4-methoxyindole

sodium cyanoborohydride

→

4-methoxyindoline

Rendimiento 54.2%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Otroto come to room temperature
4. 4
   OtroThe solvent was removed under vacuum
5. 5
   Lavadowashed with sodium carbonate solution, water and finally with brine
6. 6
   OtroThe organic layer was evaporated
7. 7
   Otrothe resulting product was purified on a silica gel column
8. 8
   Lavadoeluting with ethyl acetate:dichloromethane (5:95)

Procedimiento

4-methoxyindole (0.735 g) was dissolved in acetic acid (25 ml) and cooled in an ice bath. To this solution was added sodium cyanoborohydride (0.942 g) in portions. After the addition was complete, the solution was allowed to come to room temperature and the solution was stirred for an hour. The solvent was removed under vacuum and the residue was taken up in ethyl acetate, washed with sodium carbonate solution, water and finally with brine. The organic layer was evaporated and the resulting product was purified on a silica gel column eluting with ethyl acetate:dichloromethane (5:95) to give 0.404 g of 4-methoxyindoline.

Fuente