Triacetoxyperiodinane → 4-[3-(Trifluoromethyl)phenyl]cyclohexanone

HRID 1497020Notes

Reaction equation

HRID 1497020 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[H][H].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CCOC(C)=O.C(Cl)Cl.[Pd]>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 83261102HCID 83261102, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 832612274-[3-(Trifluoromethyl)phenyl]cyclohexanoneYield 42.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 3C (650 mg, 2.71 mmol) in EtOAc (10 mL) was added Pd/C (0.15 g, 0.27 mmol) in a pressure bottle. The mixture was stirred under 45 psi of hydrogen for 16 h. The catalyst was carefully filtered under nitrogen and the solvent was removed under vacuum. The residue was dissolved in DCM (10 mL) and Dess-Martin periodinane (1.26 g, 2.98 mmol) was added as one single portion. The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with DCM, washed with brine, dried over Na2SO4, filtered and concentrated. The crude was purified by flash chromatography on a 24 g cartridge with 0 to 100% EtOAc in hexanes over 15 min to give Intermediate 3D (276 mg, 1.14 mmol, 42.1% yield). LCMS, RT=2.01 min (Method B).

Workup

  1. filtrationThe catalyst was carefully filtered under nitrogen
  2. customthe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in DCM (10 mL)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was purified by flash chromatography on a 24 g cartridge with 0 to 100% EtOAc in hexanes over 15 min

Sources & evidence

ORD record
ord-f3d76ce786d242a099dd42e4cd4366fc
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

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