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Ethyl Acetate → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrile

HRID 2235735
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2235735
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1)[CH:9]=O.[C:20]([CH2:22]P(=O)(OCC)OCC)#[N:21].C(OCC)(=O)C>C1COCC1.O>[CH3:4][O:5][C:6]1[CH:7]=[C:8](/[CH:9]=[CH:22]/[C:20]#[N:21])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 75676Diethyl (cyanomethyl)phosphonateHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Produkt 1

HCID 66839440(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylonitrileAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A lithium hydroxide monohydrate powder (2.23 g) was added to a suspension of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (10 g) and diethyl cyanomethylphosphonate (8.2 g) in THF (50 ml) under ice-cooling, and the reaction solution was stirred at the same temperature for one hour. Ethyl acetate (200 mL) and water were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered through a silica gel pad (carrier: Chromatorex™ NH). The filtrate was concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate and hexane, and the crystals were collected by filtration. The resulting crystals were dried under reduced pressure to obtain 7.49 g of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered through a silica gel pad (carrier: Chromatorex™ NH)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was crystallized from ethyl acetate and hexane
  8. filtrationthe crystals were collected by filtration
  9. customThe resulting crystals were dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbc376c2af24499eaea6ae27618569c1
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07713993B2

Notizen zur Reaktion

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