Cesium carbonate → HCID 88531363, compound

HRID 1619166Notes

Reaction equation

HRID 1619166 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].[CH2:17]([O:20]/[N:21]=[C:22](/[C:24]1[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[CH:26][C:25]=1[CH3:32])\[CH3:23])[CH2:18][CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:30][C:28]1[CH:29]=[C:24](/[C:22](=[N:21]/[O:20][CH2:17][CH2:18][CH3:19])/[CH3:23])[C:25]([CH3:32])=[CH:26][C:27]=1[O:31][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]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 9925856(E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylateHCID 140584041HCID 140584041, compound

Product 1

HCID 88531363HCID 88531363, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (E)-methyl 2-(2-(bromomethyl)phenyl)-3-methoxyacrylate (1.0 g, 3.5 mmol) and (E)-1-(4-hydroxy-2,5-dimethylphenyl)ethanone propyloxime (0.6 g, 4.2 mmol) obtained in Step 5 in 20 mL of acetonitrile (CH3CN) was added cesium carbonate (1.7 g, 5.2 mmol), followed by stirring at room temperature for 3 hours. The reaction solvent was removed by concentration in a vacuum. 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 to remove the solvent. The concentrate was purified through silica gel chromatography to afford (E)-methyl 2-(2-((2,5-dimethyl-4-((E)-1-(propoxyimino)ethyl)phenoxy)methyl)phenyl)-3-methoxyacrylate as a white oil (0.88 g, yield 71%).

Workup

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

Sources & evidence

ORD record
ord-7aba1687b45240fe90c04a135de878d8
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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