Dimethylformamide → 6,6-Dimethyl-3-(3-(trifluoromethyl)phenylamino)cyclohex-2-enone

HRID 517175Notes

Reaction equation

HRID 517175 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][C:5](=O)[CH2:4][C:3]1=[O:9].[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.CN(C)C=O>O.CO>[CH3:1][C:2]1([CH3:10])[C:3](=[O:9])[CH:4]=[C:5]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([C:12]([F:11])([F:20])[F:21])[CH:14]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 73753-(Trifluoromethyl)anilineHCID 1363601,3-Cyclohexanedione, 4,4-dimethyl-HCID 2733225Ytterbium triflate

Product 1

HCID 867322966,6-Dimethyl-3-(3-(trifluoromethyl)phenylamino)cyclohex-2-enone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,4-dimethylcyclohexane-1,3-dione (563 mg, 4.02 mmol), 3-(trifluoromethyl)aniline (500 μL, 645 mg, 4.02 mmol), Ytterbium(III) trifluormethanesulfonate (12.5 mg, 20 μmol, 0.5 mol %) and N,N-dimethylformamide (2.5 mL) is stirred at room temperature over night. Methanol and water are added and the mixture is filtered. The precipitate is washed with water and dried under reduced pressure. Yield: 654 mg; ESI mass spectrum [M+H]+=284, Retention time HPLC: 1.18 min (Z005—001).

Workup

  1. filtrationthe mixture is filtered
  2. washThe precipitate is washed with water
  3. customdried under reduced pressure
  4. custom1.18 min (Z005—001)

Sources & evidence

ORD record
ord-f45bb5638b39415988f1d003208cf4c6
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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