Water → HCID 76714290, compound

HRID 339136Notes

Reaction equation

HRID 339136 reaction equation
[OH2:1].[F:2][C:3]([F:18])([F:17])[C:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([F:16])[CH:7]=1)=O.O.[N:20]1C=CC=CC=1>C(O)C>[F:2][C:3]([F:18])([F:17])[C:4]([C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([F:16])[CH:7]=1)=[N:20][OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 86653080HCID 86653080, compound

Product 1

HCID 76714290HCID 76714290, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.00 g (15.37 mmol) of 2,2,2-trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone hydrate from Stage 1 were stirred in a mixture of 37.3 ml of pyridine and 26.9 ml of ethanol, and stirred at reflux temperature for approx. 18 hours. After cooling, the entire reaction mixture was admixed with water and then concentrated under reduced pressure. The remaining residue was purified by means of column chromatography using silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm; cyclohexane/acetone gradient) to obtain 2.18 g (51.5% of theory) of 2,2,2-trifluoro-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone oxime as a syn/anti isomer mixture.

Workup

  1. temperatureat reflux temperature for approx. 18 hours
  2. temperatureAfter cooling
  3. customthe entire reaction mixture
  4. concentrationconcentrated under reduced pressure
  5. customThe remaining residue was purified by means of column chromatography

Sources & evidence

ORD record
ord-16c2845c224f47d09ccc7efdbaabe7a4
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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