Reaktion #4448

Reaktionsgleichung

2-benzyl-4-(4-pyridyl)thiazole

potassium permanganate

→

1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone

Ausbeute 18.8%

Lösungsmittel

benzene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe biphasic mixture was heated
2. 2
   Temperaturat reflux for 15 hours
3. 3
   TemperaturAfter cooling the organic layer
4. 4
   Sonstigewas separated
5. 5
   Einengenconcentrated
6. 6
   Filtrationfiltered through silica gel
7. 7
   Einengenconcentrated
8. 8
   Sonstigechromatographed (ethyl acetate/hexane as eluant)
9. 9
   SonstigeRecrystallization from ethyl acetate/hexane

Vorschrift

To a mixture of 2-benzyl-4-(4-pyridyl)thiazole (3.00 g, 0.01 mol) and potassium permanganate (3.16 g, 0.02 mol) in benzene (30 mL) and water (60 mL) was added tetrahexyl ammonium iodide (0.96 g, 0.02 mol). The biphasic mixture was heated at reflux for 15 hours. After cooling the organic layer was separated and concentrated. The residue was taken up in ethyl acetate, filtered through silica gel, concentrated and chromatographed (ethyl acetate/hexane as eluant). Recrystallization from ethyl acetate/hexane afforded 1-phenyl-1-[4-(4-pyridyl)-2-thiazolyl]methanone (0.50 g, 11%). mp. 135°-136° C.

Quelle