Triacetoxyperiodinane → 1-(3,5-Dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-one

HRID 916015Notes

Reaction equation

HRID 916015 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([OH:33])[C:11]([O:29][CH2:30][O:31][CH3:32])([C:25]([F:28])([F:27])[F:26])[CH2:12][C:13]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])([CH3:15])[CH3:14])[CH:5]=[C:6]([CH3:8])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[CH3:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10](=[O:33])[C:11]([O:29][CH2:30][O:31][CH3:32])([C:25]([F:26])([F:27])[F:28])[CH2:12][C:13]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])([CH3:15])[CH3:14])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 589599681-(3,5-Dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-ol

Product 1

HCID 589599341-(3,5-Dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-oneYield 61.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 137 mg (0.29 mmol) of 1-(3,5-dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-ol (Example 12) in dichloromethane was added 350 mg (0.82 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane). After 1 hour, the reaction was quenched with saturated sodium bicarbonate, and filtered through diatomaceous earth, washing with EtOAc. The organic layer was separated and the basic aqueous phase extracted with two 5 mL portions of EtOAc. The combined organic layers were washed with 5 mL of saturated aqueous sodium bicarbonate, three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified on a prep plate (2 mm, silica gel, EtOAc-hexanes (1:9), 3×developed) to afford 84 mg (61%) of 1-(3,5-dimethylphenyl)-5-(5-fluoro-2-methoxyphenyl)-3-methoxymethoxy-5-methyl-3-trifluoromethylhexan-2-one.

Workup

  1. customthe reaction was quenched with saturated sodium bicarbonate
  2. filtrationfiltered through diatomaceous earth
  3. washwashing with EtOAc
  4. customThe organic layer was separated
  5. extractionthe basic aqueous phase extracted with two 5 mL portions of EtOAc
  6. washThe combined organic layers were washed with 5 mL of saturated aqueous sodium bicarbonate, three 5 mL portions of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified on a prep plate (2 mm, silica gel, EtOAc-hexanes (1:9), 3×developed)

Sources & evidence

ORD record
ord-b99686befcd84b5591b973a90cbcdc33
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

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