1,1,1-Trifluoro-2-propanol → HCID 13440335, compound

HRID 1961426Notes

Reaction equation

HRID 1961426 reaction equation
[H-].[Na+].[F:3][C:4]([F:9])([F:8])[CH:5]([OH:7])[CH3:6].F[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1>CN(C=O)C.O>[F:3][C:4]([F:9])([F:8])[CH:5]([O:7][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)[CH3:6]

Participants

6

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 145174-FluorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 13440335HCID 13440335, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydride (297 mg, 12.4 mmol) was suspended in DMF (3 ml) at 0° C. 1,1,1-trifluoropropan-2-ol (500 μl, 5.52 mmol) was added slowly and the reaction was stirred for 15 minutes at 0° C. before addition of 4-fluorobenzonitrile (500 mg, 4.13 mmol). The mixture was allowed to reach room temperature and was then stirred at 50° C. for 20 hours. The reaction was cooled, diluted with water (75 ml) and extracted with EtOAc (4*20 ml). Combined organics were washed with water (20 ml), dried over MgSO4 and evaporated. The product was purified by flash chromatography using pet.ether/EtOAc (8:1) as eluent to give 690 mg (78%) of the title compound as a clear liquid.

Workup

  1. customto reach room temperature
  2. temperatureThe reaction was cooled
  3. extractionextracted with EtOAc (4*20 ml)
  4. washCombined organics were washed with water (20 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-832f76b97e4341358fd9d1c28a8293f9
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

Loading…