Potassium Carbonate → HCID 67955390, compound

HRID 1619178Notes

Reaction equation

HRID 1619178 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9](=[O:13])[CH2:10][O:11][CH3:12])=[C:4]([CH3:14])[CH:3]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1/[C:23](=[CH:28]\[O:29][CH3:30])/[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:30][O:29]/[CH:28]=[C:23](\[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([C:9](=[O:13])[CH2:10][O:11][CH3:12])=[CH:6][C:7]=1[CH3:8])/[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylateHCID 67955922HCID 67955922, compound

Product 1

HCID 67955390HCID 67955390, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 30 mL of acetonitrile (CH3CN), 0.3 g (1.55 mmol) of 1-(4-hydroxy-2,5-dimethylphenyl)-2-methoxyethanone obtained in Step 1 was reacted for 4 hours with 0.44 g (1.55 mmol) of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate in the presence of 20.45 g (2.1 eq) of potassium carbonate under reflux. After completion of the reaction, the solvent was removed at a reduced pressure and the residue was stirred in water (30 mL) and extracted twice with 30 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum, followed by purification with silica gel to afford 0.47 g of (E)-methyl 3-methoxy-2-(2-((4-(2-methoxyacetyl)-2,5-dimethylphenoxy)methyl)phenyl)acrylate as a white solid (yield: 76%).

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. customthe solvent was removed at a reduced pressure
  4. extractionextracted twice with 30 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. customfollowed by purification with silica gel

Sources & evidence

ORD record
ord-d114d7ac4d5640e8a76ee244e7b68fc1
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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