Pyridine → 4,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oxime

HRID 386748Notes

Reaction equation

HRID 386748 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([OH:24])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=O.Cl.[NH2:28][OH:29].N1C=CC=CC=1>C(O)C.C(OC)(C)(C)C>[F:1][C:2]([F:26])([F:25])[C:3]([OH:24])([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=[N:28][OH:29]

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866433794,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one

Product 1

HCID 866433804,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oximeYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 4,4,4-trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one (1.0 g), hydroxylamine hydrochloride (0.28 g) and pyridine (0.42 g) in ethanol (10 mL) was heated to reflux for 5 hours. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to yield 4,4,4-trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one oxime (1.0 g).

Workup

  1. temperatureto reflux for 5 hours
  2. washthe solution was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a71517224ae149a8994d67e47a7c068f
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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