Reaktion #413326

Reaktionsgleichung

Pyridinium dichromate

5-(6-hydroxyhexyl)-imidazo[1,5-a]pyridine

water

→

5-(5-carboxypentyl)-imidazo[1,5-a]pyridine

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with methylene chloride (5×20 ml)
2. 2
   WaschenThe organic extracts are washed with 1 N sodium hydroxide
3. 3
   ExtraktionAcidification of the aqueous phase to pH=6, extraction with methylene chloride
4. 4
   Trocknendrying over sodium sulfate/magnesium sulfate

Vorschrift

Pyridinium dichromate (0.94 g) is added as a solid to a solution of 5-(6-hydroxyhexyl)-imidazo[1,5-a]pyridine (123 mg) in 10 ml of N,N-dimethylformamide at 25° under nitrogen. The solution is stirred for 6 hours, poured into 150 ml of water and extracted with methylene chloride (5×20 ml). The organic extracts are washed with 1 N sodium hydroxide. Acidification of the aqueous phase to pH=6, extraction with methylene chloride and drying over sodium sulfate/magnesium sulfate yields 5-(5-carboxypentyl)-imidazo[1,5-a]pyridine of Example 2 melting at 145°-146°.

Quelle