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

HRID 1387331Notes

Reaction equation

HRID 1387331 reaction equation
C(O)CC.Cl.[CH3:6][O:7][NH2:8].[CH3:9][C:10]1[CH:14]=[C:13]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:23][O:24][C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=2[CH3:32])=O)[O:12][N:11]=1>O>[CH3:6][O:7][N:8]=[C:15]([C:13]1[O:12][N:11]=[C:10]([CH3:9])[CH:14]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][O:24][C:25]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=1[CH3:32]

Participants

5

Reactant 3

HCID 10311-PropanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 226246042-(2,5-Dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone

Product 1

HCID 542536932-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone O-methyloximeYield 42.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

n-Propanol (2 ml) and methoxyamine hydrochloride (0.25 g, 3 mmol) were added to 2-(2,5-dimethylphenoxymethyl)-phenyl 3-methylisoxazol-5-yl ketone (0.33 g, 1 mmol), and the mixture was stirred under reflux for 15 hours. After completion of the reaction, water (200 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 (ethyl acetate/n-hexane) to give isomer A (0.18 g, 51.4%, as colorless crystals) and isomer B (0.15 g, 42.8%, as colorless crystals) of 2-(2,5-dimethylphenoxymethyl)phenyl 3-methylisoxazol-5-yl ketone O-methyloxime. One of the isomers A and B is the E-isomer and the other is Z-isomer.

Workup

  1. temperatureunder reflux for 15 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 (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-7881537b233f420588e3da7e8c2644e1
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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