Cesium carbonate → (E)-methyl 2-(2-((4-formyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate

HRID 1619172Notes

Reaction equation

HRID 1619172 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11].[OH:17][C:18]1[C:25]([CH3:26])=[CH:24][C:21]([CH:22]=[O:23])=[C:20]([CH3:27])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:22]([C:21]1[C:20]([CH3:27])=[CH:19][C:18]([O:17][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2/[C:9](=[CH:14]\[O:15][CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[C:25]([CH3:26])[CH:24]=1)=[O:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylateHCID 128272904-Hydroxy-2,5-dimethyl-benzaldehyde

Product 1

HCID 86666585(E)-methyl 2-(2-((4-formyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylateYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (1.0 g, 3.5 mmol) was reacted with 4-hydroxy-2,5-dimethylbenzaldehyde (0.6 g, 4.2 mmol) at room temperature for 3 hours in 20 mL of acetonitrile (CH3CN) in the presence of cesium carbonate (1.7 g, 5.2 mmol) with stirring. After concentration in a vacuum to remove the reaction solvent, the residue was stirred in water (20 mL) and the aqueous layer was extracted twice with 20 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in a vacuum. The residue was purified by silica gel chromatography to afford (E)-methyl 2-(2-((4-formyl-2,5-dimethylphenoxy)methyl)phenyl)-3-methoxyacrylate as a white solid (0.88 g, yield 71%).

Workup

  1. concentrationAfter concentration in a vacuum
  2. customto remove the reaction solvent
  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 layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in a vacuum
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b03c03705ed244fc8fd0e0a1eaf3d1eb
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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