Dimethyl Sulfate → HCID 54390956, Verbindung

HRID 1720562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720562
[OH-].[Na+].[N:3]([O:5][CH2:6]CCC)=O.[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][C:18]#[N:19].S(OC)(OC)(=O)=O>O.C1(C)C=CC=CC=1.CC(C)=O>[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([C:18]#[N:19])=[N:3][O:5][CH3:6]

Komponenten

8

Edukt 4

HCID 6497Dimethyl SulfateHCID 10996Butyl nitriteHCID 14798Sodium Hydroxide2×HCID 11118528HCID 11118528, Verbindung

Produkt 1

HCID 54390956HCID 54390956, VerbindungAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

95% Sodium hydroxide (0.32 g, 7.5 mmol), acetone (5 ml) and butyl nitrite (0.62 g, 6 mmol) were added to 2-(2,5-dimethylphenoxymethyl)benzyl cyanide (1.26 g, 5 mmol). The mixture was stirred at room temperature for 2 hours. Dimethyl sulfate (0.95 g, 7.5 mmol) was added, and the mixture was stirred under ice-cooling for 10 minutes and at room temperature for 1 hour. After completion of the reaction, toluene (10 ml) and 1N aqueous sodium hydroxide solution (10 ml) were added, and the mixture was stirred at room temperature for 1 hour. After stirring, water (100 ml) was added. The mixture was extracted with ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (1.29 g, Yield: 87.6%, E/Z=13/87).

Aufarbeitung

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 10 minutes and at room temperature for 1 hour
  3. additionwere added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringAfter stirring
  6. extractionThe mixture was extracted with ether (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b8b604332f514944b1ec921d811b96d8
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506358

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