Réaction #1168917

Équation de réaction

5-[3-(acetyloxy)propylthio]imidazo[1,2-a]pyridine

m-chloroperbenzoic acid

→

5-[3-(acetyloxy)propylsulfinyl]imidazo[1,2-a]pyridine

Rendement 34.6%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was further stirred under ice-
3. 3
   Températurecooling for 1.5 hours
4. 4
   LavageThe reaction mixture was washed in turn with an aqueous 20% sodium bisulfite solution
5. 5
   Séchagean aqueous saturated sodium bicarbonate solution and dried
6. 6
   workup.DISTILLATIONAfter the solvent was distilled off
7. 7
   Autrethe residue was purified by column chromatography [eluent:hexane/acetone (1:1)]

Mode opératoire

To a solution of 5-[3-(acetyloxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 3.99 mmoles) in chloroform (25 ml) was added m-chloroperbenzoic acid (1.47 g, 5.96 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 1.5 hours. The reaction mixture was washed in turn with an aqueous 20% sodium bisulfite solution and an aqueous saturated sodium bicarbonate solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent:hexane/acetone (1:1)] to obtain 0.19 g of 5-[3-(acetyloxy)propylsulfinyl]imidazo[1,2-a]pyridine (Compound 177) (34.6%, yellow oily product) and 0.19 g of 5-(acetyloxy)propylsulfonyl]imidazo[1,2-a]pyridine (Compound 178) (16.5%, yellow oily product).

Source