3,3,3-Trifluoro-2-[1-(5-fluoro-2-methoxyphenyl)cyclopropylmethyl]propane-1,2-diol → 1,1,1-Trifluoro-3-[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]propan-2-one

HRID 1988176Notes

Reaction equation

HRID 1988176 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([CH2:7][C:8]1([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[CH2:10][CH2:9]1)([OH:6])CO.I([O-])(=O)(=O)=O.[Na+]>CO>[F:21][C:2]([F:1])([F:20])[C:3](=[O:6])[CH2:7][C:8]1([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[O:18][CH3:19])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 223984903,3,3-Trifluoro-2-[1-(5-fluoro-2-methoxyphenyl)cyclopropylmethyl]propane-1,2-diolHCID 23667635Sodium periodate

Product 1

HCID 223984731,1,1-Trifluoro-3-[1-(5-fluoro-2-methoxyphenyl)cyclopropyl]propan-2-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 310 mg (1.01 mmol) of 3,3,3-trifluoro-2-[1-(5-fluoro-2-methoxyphenyl)cyclopropylmethyl]propane-1,2-diol in 15 mL of MeOH was added 1.5 g (7.01 mmol) of sodium periodate. After 7 hours, the mixture was concentrated and the residue diluted with hexanes and filtered through diatomaceous earth. The crude residue was chromatographed on silica gel using hexanes to load the sample and then eluting with EtOAc-hexanes (0:100, then 0.25:99.75, then 0.5:99.5, then 1:99) to afford 200 mg of the title compound as a clear oil.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue diluted with hexanes
  3. filtrationfiltered through diatomaceous earth
  4. customThe crude residue was chromatographed on silica gel
  5. washeluting with EtOAc-hexanes (0:100

Sources & evidence

ORD record
ord-b2214ef7e86a4ac49564235e3f662a9d
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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