Trifluoroacetic acid → HCID 4715050, compound

HRID 2360517Notes

Reaction equation

HRID 2360517 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH:10]([CH3:12])[CH3:11])=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>O>[CH2:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12644950HCID 12644950, compound

Product 1

HCID 4715050HCID 4715050, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

1.9 g 1-(4-methoxy-phenyl)-2-methyl-propan-1-ol are dissolved in 30 ml dissolved, cooled to 0° C. and mixed with 3.37 ml triethylsilane. The mixture is stirred for 10 minutes and then 1.62 ml trifluoroacetic acid are added. Within 1 hour the mixture is heated to 10° C., then the reaction is stopped by the addition of water and the phases are separated. The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and then dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5 to 80:20).

Workup

  1. dissolutiondissolved
  2. temperatureWithin 1 hour the mixture is heated to 10° C.
  3. customthe phases are separated
  4. washThe organic phase is washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  5. customdried on magnesium sulphate
  6. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5 to 80:20)

Sources & evidence

ORD record
ord-2b1bef8475834188ae89eda5ffcf128e
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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