Dimethylformamide dimethyl acetal → 1-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(dimethylamino)prop-2-en-1-one

HRID 1097412Notes

Reaction equation

HRID 1097412 reaction equation
[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.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:16](=[O:18])[CH:17]=[CH:21][N:22]([CH3:24])[CH3:23])[CH:9]=[CH:10][C:11]=2[O:12][CH:13]([F:15])[F:14])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 189497631-(3-Cyclopropylmethoxy-4-difluoromethoxyphenyl)ethanone

Product 1

HCID 668122341-[3-(Cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(dimethylamino)prop-2-en-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene, dissolved were 1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]ethanone (10 g, 39 mmol) and DMFDMA (N,N-dimethyl formamide dimethyl acetal) (13.9 g, 117 mmol), and the mixture was heated under reflux. The reaction mixture was extracted with EA, and the extract was washed twice with brine, dried over MgSO4, filtered and evaporated under reduced pressure to remove solvent. The mixture was purified via column chromatography (MC/MeOH=10/1) to obtain 1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-3-(dimethylamino)prop-2-en-1-one (11 g, 92%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. extractionThe reaction mixture was extracted with EA
  4. washthe extract was washed twice with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto remove solvent
  9. customThe mixture was purified via column chromatography (MC/MeOH=10/1)

Sources & evidence

ORD record
ord-7a9ad909660a4a199a35d7832d141e0e
Source dataset
uspto-grants-2012_03
Patent number
US08143262B2

Reaction notes

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