Water → 4-hydroxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one

Participants

Reaction Steps

In 3 ml of chloroform were dissolved 0.18 g of 3-acetyl-4-hydroxy-2H-1-benzopyran-2-one, 0.17 g of 3-(methoxyacetylamino)benzaldehyde and 60 mg of piperidine, and the solution was heated under refluxing for 1 hour and 10 minutes while water was removed with a Soxhlet's extractor filled with a molecular sieve. After cooling to room temperature, the reaction solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and fractions corresponding to Rf=0.3 were collected by thin layer chromatography (silica gel, chloroform (containing 2% methanol)), and concentrated to obtain 0.30 g of 4-hydroxy-3-[3-[3-(methoxyacetylamino)phenyl]-1-oxo-2-propenyl]-2H-1-benzopyran-2-one [Compound No. (21d)].

Provenance & Evidence