Ethyl Acetate → HCID 53754295, compound

After 2-[(3-methyl-4-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.525 g was dissolved in pyridine 5 ml, propionyl chloride 0.218 ml was added, and the mixture was refluxed for 1.5 hours. The reaction mixture was cooled to room temperature, ethyl acetate 50 ml was added, and the mixture was washed with 2N-hydrochloric acid 50 ml, saturated salt solution 50 ml, saturated sodium bicarbonate solution 50 ml, and saturated sodium chloride solution 50 ml. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 350 ml of hexane:ethyl acetate=1:1) and concentrated to dryness at a temperature of 40° C. under reduced pressure to obtain crystals. The crystals were recrystallized with ethyl acetate 2 ml/hexane 5 ml and filtered. The crystals were dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure to obtain the desired compound 322.9 mg.

1. temperaturethe mixture was refluxed for 1.5 hours
2. washthe mixture was washed with 2N-hydrochloric acid 50 ml, saturated salt solution 50 ml, saturated sodium bicarbonate solution 50 ml, and saturated sodium chloride solution 50 ml
3. concentrationconcentrated under reduced pressure
4. washThe residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 350 ml of hexane:ethyl acetate=1:1)
5. concentrationconcentrated to dryness at a temperature of 40° C. under reduced pressure
6. customto obtain crystals
7. customThe crystals were recrystallized with ethyl acetate 2 ml/hexane 5 ml
8. filtrationfiltered
9. dry with materialThe crystals were dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure

ORD record

ord-f3e529f636cf4f97bff149f8a8717cf5

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143779