2-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol → 1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one

HRID 457270Notes

Reaction equation

HRID 457270 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([C:14]([F:17])([F:16])[F:15])([OH:13])CO)[CH:7]=1.I([O-])(=O)(=O)=O.[Na+]>CO.CCOCC.CCCCCC>[F:17][C:14]([F:15])([F:16])[C:10](=[O:13])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:20][CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 219489282-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanolHCID 23667635Sodium periodate

Product 1

HCID 100849201,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-oneYield 87.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.9 g (15.8 mmol) of the above 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol in 100 mL of MeOH was added 10 g (45.9 mmol) of sodium periodate. The mixture was stirred for 4 hours and was then diluted with 100 mL of ether and 100 mL of hexane, filtered through diatomaceous earth and concentrated in vacuo. The crude residue was dissolved in hexane and passed through a pad of silica gel, eluting first with hexane then with EtOAc-hexane (2:98, then 4:96) to afford 3.85 g (87%) of the title compound as a clear oil.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude residue was dissolved in hexane
  4. washeluting first with hexane

Sources & evidence

ORD record
ord-0daa08e4aae8483fb103116f3649a6e4
Source dataset
uspto-grants-2007_03
Patent number
US07186864B2

Reaction notes

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