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

HRID 1387364Notes

Reaction equation

HRID 1387364 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-toluene-sulfonate (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 acetatein-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 acetatein-hexane)

Sources & evidence

ORD record
ord-9302d05d1c4b4f10988068dff16d9977
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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