Potassium Carbonate → HCID 57934053, compound

HRID 1950617Notes

Reaction equation

HRID 1950617 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:7]([OH:9])[CH:8]=1.F[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:7]([CH:8]=1)[O:9][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 113569695-methoxy-2-(4-methoxybenzyl)phenol

Product 1

HCID 57934053HCID 57934053, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was synthesized by referring to Synthesis, 1991, (1), 63. To a solution of 5-methoxy-2-(4-methoxybenzyl)phenol (1.9 g) in N,N-dimethylacetamide (6 ml) was added 4-fluorobenzaldehyde (960 mg) and potassium carbonate (1.3 g), and the solution was refluxed for 1 hour and 10 minutes. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.0 g).

Workup

  1. customThe title compound was synthesized
  2. customby referring to Synthesis, 1991, (1), 63
  3. temperaturethe solution was refluxed for 1 hour and 10 minutes
  4. extractionThe solution was extracted with ethyl acetate
  5. washsequentially washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-b8a984355efa4d4aab4fdc4184de86f9
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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