Reacción #68860

Ecuación de reacción

indole-5-carbaldehyde

1,4-diaza-bicyclo[2.2.2]octane

EtOAc

water

→

title compound

Rendimiento 46.0%

1-Methyl-1H-indole-5-carbaldehyde

Rendimiento 46.0%

Disolventes

dimethyl carbonate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature (rt)
2. 2
   Extracciónthe aqueous phase was extracted with EtOAc (3×10 mL)
3. 3
   LavadoThe combined organic extracts were washed with brine (1×20 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   Concentraciónconcentrated

Procedimiento

A solution of indole-5-carbaldehyde (0.5 g) in dimethyl carbonate (5 mL) was treated with 1,4-diaza-bicyclo[2.2.2]octane (38 mg). The resulting mixture was heated to 90° C. for 5 h and cooled to room temperature (rt). EtOAc (10 mL) and water (10 mL) were added, and the aqueous phase was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine (1×20 mL), dried (MgSO4), and concentrated. Chromatography of the residue (0-50% EtOAc-hexanes) gave the title compound as a white solid (46%).

Fuente