Reaktion #68860

Reaktionsgleichung

indole-5-carbaldehyde

1,4-diaza-bicyclo[2.2.2]octane

EtOAc

water

→

title compound

Ausbeute 46.0%

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

Ausbeute 46.0%

Lösungsmittel

dimethyl carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature (rt)
2. 2
   Extraktionthe aqueous phase was extracted with EtOAc (3×10 mL)
3. 3
   WaschenThe combined organic extracts were washed with brine (1×20 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

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%).

Quelle