Benzonitrile → HCID 59272919, Verbindung

HRID 1696192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696192
[NH2:1][C@@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6].[C:9](#N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].[Zn+2].[Br-]>[CH3:6][S:5][CH2:4][CH2:3][C@@H:2]1[CH2:7][O:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:1]1

Komponenten

4

Edukt 2

HCID 7505BenzonitrileHCID 7000073D-Methioninol

Produkt 1

HCID 59272919HCID 59272919, VerbindungAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10421208Zinc bromideKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of (R)-methioninol (4.95 g), benzonitrile (8.3 mL) and zinc bromide (250 mg) was stirred at 120° C. for 90 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was washed with water and brine, dried over magnesium sulfate and filtered again. The filtrate was concentrated in vacuo, and the resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1) to give (R)-4-(2-methylthioethyl)-2-phenyl-4,5-dihydrooxazole (3.94 g, yield: 48.6%) as a colorless oil.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-4dadba22a1754b22b92db7e7dde409fe
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163759B2

Notizen zur Reaktion

Wird geladen…