Heptane → 3-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-ol

HRID 1095875Notes

Reaction equation

HRID 1095875 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:20])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)=[O:12].[F:21][C:22]([Si](C)(C)C)([F:24])[F:23].O.O.O.[F-].C[N+](C)(C)C.CCCCCCC>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:20])[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=1)([OH:12])[C:22]([F:24])([F:23])[F:21]

Participants

6

Reactant 4

HCID 8900HeptaneHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2735143Tetramethylammonium fluoride trihydrate (9CI)2×HCID 86645943HCID 86645943, compound

Product 1

HCID 574212633-(2-Chloro-4-methoxy-phenyl)-2-(2-chloro-pyridin-4-yl)-1,1,1-trifluoro-butan-2-olYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-on (14.75 g, 0.0475 mol) in tetrahydrofuran (900 ml) was added a solution of (trifluoromethyl)-trimethylsilane (14.89 g, 0.104 mol) in tetrahydrofuran (100 ml) at 0° C. (duration: 5 min.). Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.76 mmol) was added and the mixture was stirred at r.t. for 3 h. A second portion of Tetramethylammonium fluoride trihydrate 1M in THF (4.76 ml, 4.47 mmol) was added and the mixture was stirred at r.t. for 1 h. The mixture was poured in ice water and extracted twice with AcOEt. The organic phases were washed with saturated aqueous NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated to give an oil, which solidified over night. The residue was treated with heptane, filtered off and dried to give the title compound (13.85 g) as a light yellow crystalline product. MS (m/e, ISP neg. ion)=378.4 [M−H+].

Workup

  1. stirringthe mixture was stirred at r.t. for 1 h
  2. extractionextracted twice with AcOEt
  3. washThe organic phases were washed with saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil, which
  8. waitsolidified over night
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-1981f0450a194d0f8abf6b000e33de96
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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