Reacción #84199

Ecuación de reacción

ammonium chloride

indole

methylmagnesium bromide

1-naphthoylchloride

→

3-(1-naphthoyl)-1H-Indole

Rendimiento 91.0%

3-(1-naphthoyl)-1H-indole

Rendimiento 91.0%

Disolventes

ether

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter addition
2. 2
   TemperaturaThen the mixture was cooled down again to 0° C.
3. 3
   workup.ADDITIONto it was added slowly
4. 4
   TemperaturaThe resulting mixture was warmed up to room temperature
5. 5
   workup.STIRRINGstirred for 2 h at room temperature
6. 6
   workup.STIRRINGThe mixture was then stirred overnight at room temperature
7. 7
   OtroA white solid was formed
8. 8
   Filtraciónfiltered
9. 9
   Lavadowashed by ether
10. 10
    Otrodried under high vacuum

Procedimiento

To a cooled solution of indole (5.85 g, 50 mmol) in ether (50 ml) under nitrogen was added slowly a solution of methylmagnesium bromide (3M) in ether (17.5 ml). After addition, the reaction mixture was warmed up to room temperature and stirred for 2 h at room temperature. Then the mixture was cooled down again to 0° C., and to it was added slowly with stirring a solution of 1-naphthoylchloride (9.5 g, 50 mmol) in ether (50 ml). The resulting mixture was warmed up to room temperature and stirred for 2 h at room temperature followed by slow addition of saturated ammonium chloride solution (375 ml). The mixture was then stirred overnight at room temperature. A white solid was formed, filtered, washed by ether and dried under high vacuum to give 3-(1-naphthoyl)-1H-Indole 1 (12.3 g, 91%).

Fuente