1,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-ol → HCID 22475635, compound

HRID 2184073Notes

Reaction equation

HRID 2184073 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[N+](=[C:25]([C:30]([O:32][CH3:33])=[O:31])[C:26]([O:28][CH3:29])=[O:27])=[N-]>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[F:20][C:17]([F:19])([F:18])[CH2:16][N:15]([C:12]1[CH:11]=[CH:10][C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:21])([F:22])[F:1])=[CH:14][CH:13]=1)[CH:25]([C:30]([O:32][CH3:33])=[O:31])[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 2

HCID 4479111,1,1,3,3,3-Hexafluoro-2-{4-[(2,2,2-trifluoroethyl)amino]phenyl}propan-2-olHCID 5476732-Diazonio-1,3-dimethoxy-3-oxoprop-1-en-1-olate

Product 1

HCID 22475635HCID 22475635, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from step 1 (500 mg, 1.47 mmol), dimethyl diazomalonate (220 mg, 1.4 mmol, prepared via Synthetic Comm., 17 (14), 1709-16 (1987)), and rhodium acetate (65 mg, 0.015 mmol) were combined and dissolved in CH2Cl2 (12 mL). The resulting mixture was heated at reflux over 1.5 h, cooled to room temperature, and concentrated in vacuo. Purification by flash chromatography (4:1 hexanes/EtOAc) afforded the title compound as a colorless oil (626 mg, 95%). MS (ES+) m/z 472 (MH+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux over 1.5 h
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-abf9ebbdb3a9409ba7c3a3313aebc68d
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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