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

HRID 44956

Reaction equation

HRID 44956 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH3:16][N:17]([CH3:19])/[CH:18]=[CH:10]/[C:9]([C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:8]=1)=[O:11]

Participants

3

Reactant 2

HCID 676823'-(Trifluoromethyl)acetophenoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 5398493(2E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one

Conditions

Temperature
120 °C

Procedure

1-[5-(Trifluoromethyl)phenyl]ethanone (0.20 mL, 0.0013 mol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.17 mL, 0.0013 mol) were combined in a sealed tube and heated in a microwave to 120° C. for 15 minutes, the reaction was allowed to cool and was concentrated to remove the residual DMF acetal, to give (2E)-3-(dimethylamino)-1-[3-(trifluoromethyl)phenyl]prop-2-en-1-one, 0.32 gm, as a red oil, LC/MS (M+H)+: 244.

Workup

  1. temperatureto cool
  2. concentrationwas concentrated
  3. customto remove the residual DMF acetal

Sources & evidence

ORD record
ord-78cff07ab8fd46c98fbea1564b27c085
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Linked notes

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