1-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanol → 1-(3-Cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone

HRID 1097411Notes

Reaction equation

HRID 1097411 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:16]([OH:18])[CH3:17])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16](=[O:18])[CH3:17])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 592936281-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 189497631-(3-Cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanoneYield 91%

Procedure

In dry MC, dissolved was 1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanol (24 g, 93 mmol), and PCC (pyridinium chlorochromate) (30 g, 139 mmol) was added thereto. The resultant mixture was heated under reflux. The reaction mixture was filtered through Celite, and the filtrate was extracted with EA, washed twice with brine, dried over MgSO4 and filtered. After removing the solvent by evaporation under reduced pressure, the mixture was purified via column chromatography (n-hexane/MC=7/1) to obtain 1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanone (19 g, 91%).

Workup

  1. dissolutionIn dry MC, dissolved
  2. additionwas added
  3. temperatureunder reflux
  4. filtrationThe reaction mixture was filtered through Celite
  5. extractionthe filtrate was extracted with EA
  6. washwashed twice with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customAfter removing the solvent
  10. customby evaporation under reduced pressure
  11. customthe mixture was purified via column chromatography (n-hexane/MC=7/1)

Sources & evidence

ORD record
ord-ca21e6e32eff4ff29b999ea7726d3f5e
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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