Potassium Carbonate → HCID 86666592, compound

HRID 1619170Notes

Reaction equation

HRID 1619170 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17].[OH:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:27]=[O:28]>C(#N)C>[CH:27]([C:26]1[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:24]([CH:25]=1)[O:23][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])=[O:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate

Product 1

HCID 86666592HCID 86666592, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (0.35 g, 2.6 mmol) was added to a solution (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (0.5 g, 1.7 mmol) and 3-hydroxy-4-methoxybenzaldehyde (0.32 g, 2.1 mmol) in 20 mL of acetonitrile (CH3CN) which was then stirred for 6 hours under reflux. The reaction solvent was removed by vacuum concentration. The residue was stirred in water (20 mL), and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum to remove the solvent. Purification through silica gel chromatography afforded the title compound as a white oil (0.3 g, yield 49%).

Workup

  1. temperatureunder reflux
  2. customThe reaction solvent was removed by vacuum concentration
  3. stirringThe residue was stirred in water (20 mL)
  4. extractionthe aqueous layer was extracted twice with 20 mL of dichloromethane
  5. dry with materialThe organic was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customto remove the solvent
  9. customPurification through silica gel chromatography

Sources & evidence

ORD record
ord-c520ee5433504bb3b7cb289e2edefa1f
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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