Potassium Carbonate → Benzaldehyde, (dimethylamino)-

HRID 1854700Notes

Reaction equation

HRID 1854700 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:16][NH:17][CH3:18].C(O)C>CN(C)C=O.C(OCC)(=O)C>[CH3:16][N:17]([CH3:18])[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 22184060Dimethylamine ethanol

Product 1

HCID 34289Benzaldehyde, (dimethylamino)-Yield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 2-fluorobenzaldehyde (250 μL, 2.37 mmol) and potassium carbonate (328 mg, 2.37 mmol) in 5 mL of dry N,N-dimethylformamide was added dimethylamine/ethanol solution (0.65 mL, 5.6 M, 3.6 mmol) at room temperature. After being stirred at 110° C. for 12 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain the title compound as a yellow oil (299 mg, 85%).

Workup

  1. washThe solution was washed with water, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20)

Sources & evidence

ORD record
ord-699ce1e0219f4702bff22852f83f30e7
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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