Methanol → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

HRID 342182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342182
CO.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(OC([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[N:38][O:39][CH3:40])[C:34]([NH:36][CH3:37])=[O:35])C)C>[Cl-].[Na+].O>[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](=[N:38][O:39][CH3:40])[C:34]([NH:36][CH3:37])=[O:35]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 536744052-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide

Produkt 1

HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Methanol (4 ml) and pyridinium p-toluenesulfonate (0.04 g, 0.00017 mol) were added to an E/Z mixture of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-methoxyimino-N-methylacetamide (0.50 g, 0.0017 mol), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, half-saturated brine (100 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (0.34 g, Yield: 90.0%, E/Z=96/4) as a colorless oil.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (50 ml) twice
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-125ffc03e32f4c31badab379434a35ee
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856573

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