1-(4-(Trifluoromethyl)phenyl)ethan-1-one → (2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one

HRID 1715688Notes

Reaction equation

HRID 1715688 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:10]/[C:9]([C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:8][CH:7]=1)=[O:11]

Participants

3

Reactant 2

HCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5714026(2E)-3-(dimethylamino)-1-[4-(trifluoromethyl)phenyl]prop-2-en-1-one

Procedure

A solution of 4′-(trifluoromethyl)acetophenone (9.60 g, 50 mmol) in 25 ml of N,N-dimethylformamide dimethyl acetal (DMF-DMA) is stirred at 105 to 110° C. for 20 hrs. It is then cooled to room temperature, and diluted with hexanes. The resulting suspension is filtered, and the precipitate washed with hexanes to give 10.93 g of a yellow solid; mp 96.5-98° C.; MS (ESI) m/z 244.1 (M+H).

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe precipitate washed with hexanes

Sources & evidence

ORD record
ord-51a07b81ba1146519bba2161e131cda9
Source dataset
uspto-grants-2010_09
Patent number
US07799915B2

Reaction notes

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