Methanol → 3-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one

HRID 59641Notes

Reaction equation

HRID 59641 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31].[C:37]1(=O)[CH2:42][CH2:41][CH2:40][C:39](=[O:43])[CH2:38]1.CO>O>[F:26][C:27]([F:35])([F:36])[C:28]1[CH:29]=[C:30]([NH:31][C:37]2[CH2:42][CH2:41][CH2:40][C:39](=[O:43])[CH:38]=2)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 73753-(Trifluoromethyl)anilineHCID 104341,3-CyclohexanedioneHCID 2733225Ytterbium triflate

Product 1

HCID 27486303-{[3-(Trifluoromethyl)phenyl]amino}cyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ytterbiumtriflate (138 mg; 0.223 mmol) is added to a solution of m-trifluoromethylaniline (5.55 mL; 44.6 mmol) and 1,3-cyclohexanedione (5.0 g; 44.6 mmol) and the mixture is stirred at room temperature for 1 h. Methanol is added to the suspension until everything is dissolved. Water is added and the precipitate is filtered off, washed with water and dried. Yield: 10.35 g. ESI mass spectrum: [M+H]+=256; Retention time HPLC: 0.47 min (X012_S01).

Workup

  1. dissolutionis dissolved
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried
  5. custom0.47 min (X012_S01)

Sources & evidence

ORD record
ord-821953fe179f4d638b5eb4f003db0e95
Source dataset
uspto-grants-2016_09
Patent number
US09440930B2

Reaction notes

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