Acetyl chloride → HCID 54533088, compound

HRID 1856930Notes

Reaction equation

HRID 1856930 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:22](Cl)(=[O:24])[CH3:23].C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]2[C:15](=[O:16])[C:14]3[CH:17]=[CH:18][C:19]([O:21][C:22](=[O:24])[CH3:23])=[CH:20][C:13]=3[O:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 54283810HCID 54283810, compound

Product 1

HCID 54533088HCID 54533088, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 2-[(3-methyl-4-methoxyphenyl)methylene]-6-hydroxy-3(2H)- benzofuranone 0.5 g was dissolved in pyridine 5 ml, acetyl chloride 0.2 ml was added, and the mixture was refluxed for 1.5 hours. The solution was cooled to room temperature, ethyl acetate 50 ml was added, and the mixture was washed with 2N-hydrochloric acid 50 ml twice. After the ethyl acetate solution was dehydrated with anhydrous magnesium sulfate, it was 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 dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 436.6 mg.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. washthe mixture was washed with 2N-hydrochloric acid 50 ml twice
  3. concentrationwas concentrated under reduced pressure
  4. washThe residue was fractionated by silica gel column chromatography (silica gel: 50 g, eluted with solvent 500 ml of hexane:ethyl acetate=1:1)
  5. concentrationthe fraction was concentrated to dryness at a temperature of 40° C. under reduced pressure
  6. customto obtain crystals
  7. dry with materialThe crystals were dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-0d14748ddb904e138222d60116a17d45
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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