Potassium Carbonate → (R)-2-[2-(5-Fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

HRID 854167Notes

Reaction equation

HRID 854167 reaction equation
[F:1][C:2]([F:27])([F:26])[C@@:3]([CH2:17]SC1C=CC(C)=CC=1)([OH:16])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[CH3:15])([CH3:7])[CH3:6].F[B-](F)(F)F.C[O+](C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O>[F:14][C:12]1[CH:11]=[CH:10][C:9]([CH3:15])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C@:3]2([C:2]([F:27])([F:26])[F:1])[CH2:17][O:16]2)[CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 58933188(S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol

Product 1

HCID 11701812(R)-2-[2-(5-Fluoro-2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxiraneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol (1.37 g, 3.41 mmol) in 10 mL of anhydrous dichloromethane was added trimethyloxonium tetrafluoroborate (757 mg, 5.12 mmol). The resulting suspension was stirred at room temperature for 4.5 hours. A solution of potassium carbonate (1.41 g, 10.2 mmol) in 10 mL of water was then added. After 19 hours, the reaction mixture was poured into 40 mL of saturated aqueous sodium bicarbonate solution and extracted with three 50 mL portions of dichloromethane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography with silica gel (eluted with 0%-2% EtOAc-hexanes) afforded the title compound as a clear oil (731 mg, 78%).

Workup

  1. waitAfter 19 hours
  2. extractionextracted with three 50 mL portions of dichloromethane
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography with silica gel (eluted with 0%-2% EtOAc-hexanes)

Sources & evidence

ORD record
ord-9b666b83b16d4b96b05a745eaec8e9af
Source dataset
uspto-grants-2007_08
Patent number
US07256300B2

Reaction notes

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