Dimethylformamide → HCID 53864547, compound

To a solution of 2-[(4-methoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.5 g, potassium carbonate 0.58 g and dimethylformamide 5 ml, 2-bromopropane 0.306 g was added. After the mixture was refluxed for 2.5 hours, water 50 ml was added. The resulting compound was extracted with ethyl acetate 50 ml twice. The ethyl acetate solution was washed with a saturated sodium chloride solution 50 ml twice, 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 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 dissolved in ethyl acetate 1 ml and hexane 10 ml, and the solution was allowed to stand at room temperature for four hours. The precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 462.9 mg.

1. temperatureAfter the mixture was refluxed for 2.5 hours
2. extractionThe resulting compound was extracted with ethyl acetate 50 ml twice
3. washThe ethyl acetate solution was washed with a saturated sodium chloride solution 50 ml twice
4. concentrationconcentrated under reduced pressure
5. washThe residue was 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. filtrationThe precipitated crystals were filtered
9. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

ORD record

ord-589fc792f7c14fc4afbb28f7249d1201

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143779