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1-Propanol → 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone O-methyloxime

HRID 1004354
Notes
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Reaction equation

HRID 1004354 reaction equation
C(O)CC.Cl.[CH3:6][O:7][NH2:8].[O:9]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][O:23][C:24]2[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=2[CH3:31])=O)=[N:10]1>O>[CH3:6][O:7][N:8]=[C:14]([C:11]1[CH:12]=[CH:13][O:9][N:10]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:25]=1[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10311-PropanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 109028752-(2,5-Dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone

Product 1

HCID 543446862-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone O-methyloxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

n-Propanol (2 ml) and methoxyamine hydrochloride (0.50 g, 6 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone (0.64 g, 2 mmol), and the mixture was stirred under reflux for 17 hours. After completion of the reaction, water (100 ml) was added, the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel chromatography (benzene/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl isoxazol-3-yl ketone O-methyloxime (a mixture of isomers A/B) (0.55 g, 81.8%) as colorless crystals. mp. 104-108° C.

Workup

  1. temperatureunder reflux for 17 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (benzene/n-hexane)

Sources & evidence

ORD record
ord-035a1d70470e4bf191150b14f7a977cc
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048885

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes