Potassium Carbonate → N,N-diethyl-2-[(3'-formyl-2,6-dimethylbiphenyl-4-yl)oxy]acetamide

HRID 507945Notes

Reaction equation

HRID 507945 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1.Cl[CH2:19][C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:23]([N:22]([CH2:25][CH3:26])[C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[O:16])[CH:10]=2)=[C:4]([CH3:17])[CH:3]=1)[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 231116914'-Hydroxy-2',6'-dimethyl-[1,1'-biphenyl]-3-carbaldehyde

Product 1

HCID 23157212N,N-diethyl-2-[(3'-formyl-2,6-dimethylbiphenyl-4-yl)oxy]acetamideYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (0.905 g, 4.00 mmol) and 2-chloro-N,N-diethylacetamide (0.748 g, 5.00 mmol) in acetone (10 mL) was added potassium carbonate (0.663 g, 4.80 mmol), and the mixture was heated under reflux for 2 hr under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30%-70% ethyl acetate/hexane) to give the title compound (0.729 g, yield 54%) as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr under a nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (30%-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a532e67b1a1d42e098790a10c4992db5
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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