Methanol → 2-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketone O-methyloxime

HRID 279460Notes

Reaction equation

HRID 279460 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20][OH:21].[CH3:22][C:23]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][C:24]=1[O:25][CH2:26][C:27]([CH:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]1=[NH:38])(OC)C=O>CCOCC>[CH3:20][O:21][N:38]=[C:33]([C:14]1[O:17][CH:12]=[N:11][CH:10]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:32][C:27]=1[CH2:26][O:25][C:24]1[CH:39]=[C:40]([CH3:43])[CH:41]=[CH:42][C:23]=1[CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 867579072-(2,5-Dimethylphenoxymethyl)-alpha-methoxy-iminophenylacetaldehyde

Product 1

HCID 544754822-(2,5-dimethylphenoxymethyl)phenyl oxazol-5-yl ketone O-methyloximeYield 44.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

p-Toluenesulfonylmethylisocyanide (0.23 g, 1.2 mmol), potassium carbonate (0.18 g, 1.3 mmol) and methanol (2 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxy-iminophenylacetaldehyde (0.30 g, 1 mmol), and the mixture stirred under reflux for 2 hours. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with brine (80 ml) twice. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) and recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxy-methyl)phenyl oxazol-5-yl ketone O-methyloxime (0.15 g, 44.6%) as colorless crystals.

Workup

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. washthe mixture was washed with brine (80 ml) twice
  4. dry with materialThe ether 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)
  7. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-e9c62baa3625482da461529cac07e57b
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

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