Réaction #5559

Équation de réaction

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

triethylamine

3-phenylpropionyl chloride

→

desired product

Rendement 84.2%

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

Rendement 84.2%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was further stirred at room temperature for 2 hours
2. 2
   LavageThe reaction mixture was washed with an aqueous 1N sodium hydroxide solution
3. 3
   Autredried
4. 4
   workup.DISTILLATIONAfter the solvent was distilled off
5. 5
   Autrethe residue was purified by column chromatography [eluent: hexane/acetone (1:1)]

Mode opératoire

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (1.00 g, 4.80 mmoles) and triethylamine (0.80 ml, 5.74 mmoles) in methylene chloride (25 ml) was added 3-phenylpropionyl chloride (1.01 g, 5.99 mmoles) with stirring at room temperature and the mixture was further stirred at room temperature for 2 hours. The reaction mixture was washed with an aqueous 1N sodium hydroxide solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: hexane/acetone (1:1)] to obtain 1.37 g of the desired product (84.2%, yellow oily product).

Source