Benzenepropanal → 5-(3-Phenylpropylidene)-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]oxazolidine-2,4-dione

Temperature

60 °C

1.45 g (5 mmol) of 3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]oxazolidine-2,4-dione and 20 ml of ethanol were placed in a reaction flask, followed by stirring at 60° C. for 20 minutes, to dissolve the starting materials. After this mixture was kept standing to 50° C., an ethanol solution of 0.05 ml (0.5 mmol) of pyrrolidine was added. Next, an ethanol solution of 0.66 ml (5 mmol) of 3-phenylpropionaldehyde was added, followed by refluxing for 19 hours. 3.5 hours later, 0.66 ml (5 mmol) of 3-phenylpropionaldehyde and 0.05 ml (0.5 mmol) of pyrrolidine were added. After the reaction mixture was cooled, the solvent was distilled off, followed by extraction with dichloromethane and water. After the organic layer was dried with sodium sulfate, the solvent was distilled off. The residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/2) to yield 15 mg (0.74%, yellow oily substance) of the desired product.

1. dissolutionto dissolve the starting materials
2. customwas kept standing to 50° C.
3. temperatureby refluxing for 19 hours
4. temperatureAfter the reaction mixture was cooled
5. distillationthe solvent was distilled off
6. extractionfollowed by extraction with dichloromethane and water
7. dry with materialAfter the organic layer was dried with sodium sulfate
8. distillationthe solvent was distilled off
9. washThe residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/2)

ORD record

ord-a9a4cc3eb8f6467ab5783254403ff741

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840732