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

HRID 517201Notes

Reaction equation

HRID 517201 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[F:9][CH:10]([F:18])[C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].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:9][CH:10]([F:18])[C:11]1[CH:12]=[C:13]([NH:14][C:1]2[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH:2]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 104341,3-CyclohexanedioneHCID 2733225Ytterbium triflateHCID 234451193-(Difluoromethyl)aniline

Product 1

HCID 867323213-(3-(Difluoromethyl)phenylamino)cyclohex-2-enone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of cyclohexane-1,3-dione (2.00 g, 17.84 mmol), 3-(difluoromethyl)aniline (2.55 g, 17.82 mmol) and Ytterbium(III) trifluormethanesulfonate (111 mg, 178 μmol, 1.0 mol %) is stirred at room temperature for 2 h. Methanol and water are added and the mixture is extracted twice with dichloromethane. The combined organic layers are dried over Na2SO4 and concentrated under reduced pressure. The residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate). Yield: 2.76 g; ESI mass spectrum [M+H]+=237, Retention time HPLC: 0.40 min (X012_S01).

Workup

  1. extractionthe mixture is extracted twice with dichloromethane
  2. dry with materialThe combined organic layers are dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by flash chromatography on silica (gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate)
  5. custom0.40 min (X012_S01)

Sources & evidence

ORD record
ord-3561c52094af43cf89c92733a3af5e88
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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