Dimethyl Sulfate → HCID 54390956, Verbindung

HRID 1720561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720561
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:9]=1[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([C:17]#[N:18])=[N:15]O.S(OC)(OC)(=O)=O>CC(C)=O>[CH3:7][C:8]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:9]=1[O:10][CH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([C:17]#[N:18])=[N:15][O:4][CH3:1]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 85405589HCID 85405589, Verbindung

Produkt 1

HCID 54390956HCID 54390956, VerbindungAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Potassium carbonate (3.32 g, 0.024 mol) and acetone (200 ml) were added to 2-(2,5-dimethylphenoxymethyl)-α-hydroxyiminobenzyl cyanide (E/Z=15/85) (5.61 g, 0.02 mol). The mixture was stirred for 5 minutes. Then dimethyl sulfate (3.03 g, 0.024 mol) was added, and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the resulting insoluble materials were removed. To the residue obtained after evaporation under reduced pressure, toluene (50 ml) and 1N aqueous sodium hydroxide solution (50 ml) were added. The mixture was stirred for 1 hour. After stirring, water (150 ml) was added. The mixture was extracted with ether (150 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 (5.44 g, Yield: 92.4%, E/Z=15/85).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customAfter completion of the reaction
  3. customthe resulting insoluble materials were removed
  4. customTo the residue obtained
  5. customafter evaporation under reduced pressure, toluene (50 ml) and 1N aqueous sodium hydroxide solution (50 ml)
  6. additionwere added
  7. stirringThe mixture was stirred for 1 hour
  8. stirringAfter stirring
  9. additionwater (150 ml) was added
  10. extractionThe mixture was extracted with ether (150 ml)
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-082065e97dd64f719ab6147eeb135c89
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05506358

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