Methanol → 2-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime

HRID 1004388Notes

Reaction equation

HRID 1004388 reaction equation
CO.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH3:20][O:21][N:22]=[C:23]([C:37]1[CH:41]=[C:40]([CH3:42])[O:39][N:38]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][O:31]C(OCC)C>[Cl-].[Na+].O>[CH3:20][O:21][N:22]=[C:23]([C:37]1[CH:41]=[C:40]([CH3:42])[O:39][N:38]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][OH:31]

Participants

5

Reactant 3

HCID 887MethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53990473HCID 53990473, compound

Product 1

HCID 542688772-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloximeYield 92.1%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Methanol (26 ml) and pyridinium p-toluenesulfonate (0.33 g, 0.0013 mol) were added to 2-(1-ethoxyethyl)oxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime (4.14 g, 0.013 mol), and the mixture was stirred under reflux for 0.5 hour. After completion of the reaction, half-saturated brine (300 ml) was added, and the mixture was extracted with dichloromethane (100 ml) twice. The extracts were 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-hydroxymethylphenyl 5-methylisoxazol-3-yl ketone O-methyloxime (2.95 g, yield: 92.1%) as a colorless oil.

Workup

  1. temperatureunder reflux for 0.5 hour
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (100 ml) twice
  4. dry with materialThe extracts were 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-bacd65b256754670b2c225cca442fee2
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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