HCID 60026593, compound → HCID 60026369, compound

HRID 400633Notes

Reaction equation

HRID 400633 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH3:10])=[CH:5][C:4]=1[C:11]([CH3:22])([CH3:21])[CH2:12][C:13]([C:17]([F:20])([F:19])[F:18])([OH:16])CO.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>CO>[F:20][C:17]([F:18])([F:19])[C:13](=[O:16])[CH2:12][C:11]([C:4]1[CH:5]=[C:6]([S:9][CH3:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 60026593HCID 60026593, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 60026369HCID 60026369, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-methoxy-5-methylsulfanylphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol (1.5 g, 5.3 mmol) in 25 mL of methanol was added 2.4 g of lead (IV) acetate (Pb(OAc)4) and the reaction mixture was stirred until TLC indicated the reaction was complete, after several hours. The reaction mixture was then filtered through a bed of diatomaceous earth and the filtrate was concentrated in vacuo to afford 1.12 g (83.8% yield) of 1,1,1-trifluoro-4-(2-methoxy-5-methylsulfanylphenyl)-4-methylpentan-2-one.

Workup

  1. waitwas complete, after several hours
  2. filtrationThe reaction mixture was then filtered through a bed of diatomaceous earth
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d8eaca11f0c746e4b5ee622e33b6abb1
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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