Tetrahydrofuran → HCID 53886136, compound

HRID 279481Notes

Reaction equation

HRID 279481 reaction equation
C1COCC1.Cl[C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([Cl:17])=[CH:9][N:8]=1.[H-].[Na+].[CH3:20][O:21][N:22]=[C:23]([C:32]1[CH:36]=[C:35]([CH3:37])[O:34][N:33]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][OH:31]>O>[CH3:20][O:21][N:22]=[C:23]([C:32]1[CH:36]=[C:35]([CH3:37])[O:34][N:33]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][O:31][C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([Cl:17])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 110421442,5-dichloro-3-(trifluoromethyl)pyridineHCID 542688772-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime

Product 1

HCID 53886136HCID 53886136, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

THF (3 ml), 2,5-dichloro-3-trifluoromethylpyridine (0.32 g, 1.5 mmol) and 60% sodium hydride (0.05 g, 1.2 mmol) were added to 2-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime (0.25 g, 1.0 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. Water (100 ml) was added to the reaction mixture, and the mixture was extracted with ether (150 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(5-chloro-3-trifluoromethyl-2-pyridyloxymethyl)phenyl 5-methylisoxazol-3-yl ketone O-methyloxime (0.41 g, yield: 96.3%) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ether (150 ml)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-621c9bfb4712422b9e7dedc2ad1b200d
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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