Ethyl Acetate → HCID 908899, compound

After 2-[(4-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.5 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 once, saturated sodium bicarbonate solution 50 ml, and a saturated salt solution 50 ml. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate and concentrated under reduced pressure. The crude extract was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1) and the fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure to obtain crystals. The crystals were recrystallized with ethyl acetate 4 ml/hexane 10 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 251.6 mg.

1. temperaturethe mixture was refluxed for 1.5 hours
2. washthe mixture was washed with 2N-hydrochloric acid 50 ml once
3. concentrationconcentrated under reduced pressure
4. extractionThe crude extract
5. washwas fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1)
6. concentrationthe fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure
7. customto obtain crystals
8. customThe crystals were recrystallized with ethyl acetate 4 ml/hexane 10 ml
9. filtrationfiltered
10. dry with materialThe crystals were dried over phosphorous pentoxide at a temperature of 60° C. for five hours under reduced pressure

ORD record

ord-d31a4edd019247f2a8ef8c1704d103ca

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143779