Benzoyl chloride → HCID 54133674, compound

HRID 1856932Notes

Reaction equation

HRID 1856932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:14]=3[O:13]2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]=[C:12]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([O:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:21][C:14]=3[O:13]2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 53855529HCID 53855529, compound

Product 1

HCID 54133674HCID 54133674, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 2-[(3,5-dimethoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone 0.5 g was dissolved in pyridine 5 ml, benzoyl chloride 0.282 ml was added, and the mixture was refluxed for two hours. The reaction mixture was cooled to room temperature, ethyl acetate 50 ml was added and, the ethyl acetate phase was washed with 2N-hydrochloric acid 50 ml twice and with saturated sodium bicarbonate solution 50 ml. After 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 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 388.5 mg.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. washthe ethyl acetate phase was washed with 2N-hydrochloric acid 50 ml twice
  3. concentrationconcentrated 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-31433ccdf58e40cbb71d86e5f8ce7e00
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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