Benzonitrile → HCID 59272919, Verbindung
Reaktionsgleichung
[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]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
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 gas atmosphere. After cooling to room temperature, the reaction mixture was filtered and the filtrate was washed with water and a brine, dried over magnesium sulfate and filtered again. The filtrate was concentrated in vacuo and the resultant crude product was purified by a 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
- temperatureAfter cooling to room temperature
- filtrationthe reaction mixture was filtered
- washthe filtrate was washed with water
- dry with materiala brine, dried over magnesium sulfate
- filtrationfiltered again
- concentrationThe filtrate was concentrated in vacuo
- customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-447f02eb0082426faa912d1d62a8f496
- Quelldatensatz
- uspto-grants-2012_05
- Patentnummer
- US08188097B2
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