Ethyl Acetate → HCID 3741208, compound

HRID 1856940Notes

Reaction equation

HRID 1856940 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]=[CH:7][C:8]=1[O:9][CH3:10].[C:23](Cl)(=[O:26])[CH2:24][CH3:25].C(OCC)(=O)C>N1C=CC=CC=1>[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]([O:22][C:23](=[O:26])[CH2:24][CH3:25])=[CH:21][C:14]=3[O:13]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 62324Propionyl chlorideHCID 490061HCID 490061, compound

Product 1

HCID 3741208HCID 3741208, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After 2-[(3,4-dimethoxyphenyl)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 sodium bicarbonate solution 50 ml, and a 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 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 five hours under reduced pressure to obtain the desired compound 311.6 mg.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. washthe mixture was washed with 2N-hydrochloric acid 50 ml, saturated sodium bicarbonate 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 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 five hours under reduced pressure

Sources & evidence

ORD record
ord-5d282d72b94245e9b444547dc9d72ac7
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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