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 1510904Notes

Reaction equation

HRID 1510904 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-a0ac536f5a724fe4b5d2104d941f3b72
Source dataset
uspto-grants-2012_07
Patent number
US08212040B2

Reaction notes

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