1-Propanol → 2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone O-ethyloxime

HRID 1004357Notes

Reaction equation

HRID 1004357 reaction equation
C(O)CC.Cl.[CH2:6]([O:8][NH2:9])[CH3:7].[CH3:10][N:11]1[C:15]([C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[CH2:24][O:25][C:26]2[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=2[CH3:33])=O)=[CH:14][CH:13]=[N:12]1>O>[CH2:6]([O:8][N:9]=[C:16]([C:15]1[N:11]([CH3:10])[N:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][O:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=1[CH3:33])[CH3:7]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 76850O-ethylhydroxylamine hydrochlorideHCID 226246172-(2,5-Dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone

Product 1

HCID 540239772-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone O-ethyloximeYield 45.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

n-Propanol (2 ml) and ethoxyamine hydrochloride (0.18 g, 1.8 mmol) were added to 2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone (0.20 g, 0.6 mmol), and the mixture was stirred under reflux for 3 days. After completion of the reaction, water (100 ml) was added, and 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 (ethyl acetate/n-hexane) to give isomer A (0.11 g, 50.4%, as colorless crystals) and isomer B (0.10 g, 45.9%, as colorless crystals) of 2-(2,5-dimethylphenoxymethyl)phenyl 1-methylpyrazol-5-yl ketone O-ethyloxime.

Workup

  1. temperatureunder reflux for 3 days
  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 (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-6f97f33cb7cd4f2c9706596bca25624f
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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