Methanol → 3-(3-(Difluoromethyl)phenylamino)cyclopent-2-enone

HRID 927192Notes

Reaction equation

HRID 927192 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[F:8][CH:9]([F:17])[C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.CO>O>[F:8][CH:9]([F:17])[C:10]1[CH:11]=[C:12]([NH:13][C:1]2[CH2:5][CH2:4][C:3](=[O:6])[CH:2]=2)[CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 774661,3-CyclopentanedioneHCID 2733225Ytterbium triflateHCID 234451193-(Difluoromethyl)aniline

Product 1

HCID 903109643-(3-(Difluoromethyl)phenylamino)cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cyclopentane-1,3-dione (2.00 g, 20.4 mmol), 3-(difluoromethyl)aniline (2.92 g, 20.4 mmol) and Ytterbium(III) trifluormethanesulfonate (63 mg, 0.10 mmol, 0.5 mol %) is stirred at room temperature for 2 h. Methanol and water are added and the resulting precipitate is filtered and dried. Yield: 2.75 g; ESI mass spectrum: [M+H]+=224; Retention time HPLC: 0.82 min (V012_S01).

Workup

  1. filtrationthe resulting precipitate is filtered
  2. customdried
  3. custom0.82 min (V012_S01)

Sources & evidence

ORD record
ord-775d23c9a84645e28ecd4bb827e5c328
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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