Sodium Carbonate → 3-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-ol

HRID 1095924Notes

Reaction equation

HRID 1095924 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=1)=[O:20].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=1)([OH:20])[C:2]([F:4])([F:3])[F:1]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 666991512-(2-Chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-propan-1-one

Product 1

HCID 252528933-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(2-methyl-pyridin-4-yl)-butan-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trifluoromethyltrimethylsilane (2M in THF, 25.80 mL) was added at 0° C. to a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(2-methyl-pyridin-4-yl)-propan-1-one (5.98 g) in THF (100 mL) followed by the addition of tetrabutylammonium fluoride trihydrate (1.32 g). Stirring was continued for 2 hours at r.t. The reaction mixture was cooled, poured into ice and basified with sat. Na2CO3. The aqueous phase was then extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate) to give the title compound as a light yellow foam (5.96 g, 80%). MS (m/e)=360.1 [MH+].

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe aqueous phase was then extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, gradient of heptane in ethyl acetate)

Sources & evidence

ORD record
ord-ffa55898c72e49a9a4b094c5820e34fa
Source dataset
uspto-grants-2012_03
Patent number
US08138189B2

Reaction notes

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