Reaktion #74946

Reaktionsgleichung

pyridine

quinidinone

diisobutylaluminum hydride

→

quinidine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated under vacuum (25 mm Hg)
2. 2
   Sonstigeto remove the pyridine
3. 3
   workup.ADDITIONThe reaction mixture was then treated with 750 ml
4. 4
   workup.ADDITIONof a 50/50 mixture of water and ethanol
5. 5
   Temperaturafter refluxing for 2 hours
6. 6
   Temperaturcooling

Vorschrift

600 ml. anhydrous pyridine, 100 g. crystallized quinidinone, and 300 ml. 25% solution of diisobutylaluminum hydride (DIBAH) in toluene were in a reaction vessel and the reaction was allowed to proceed until the reduction was completed as indicated by thin layer chromatography. The mixture was then heated under vacuum (25 mm Hg) to remove the pyridine. The reaction mixture was then treated with 750 ml. of a 50/50 mixture of water and ethanol, and after refluxing for 2 hours and cooling, 92.7 g. of quinidine base were obtained, exhibiting a melting point of 174.5° C.

Quelle