(3,4-Difluorophenyl)acetonitrile → HCID 14838784, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[F:8].[F:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]([O:23][CH3:24])=[O:22])[CH:16]=[CH:17][CH:18]=1>C1(C)C=CC=CC=1.CC(C)([O-])C.[K+]>[C:10]([CH:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[CH:19]([C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([F:12])[CH:14]=1)[CH2:20][C:21]([O:23][CH3:24])=[O:22])#[N:11]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
Under protective gas (Ar), 3.828 g (25.0 mmol) of (3,4-difluorophenyl)acetonitrile and 0.281 mg of potassium tert-butoxide were added to 4.099 g (22.7 mmol) of methyl 3-(3-fluorophenyl)acrylate in 25.0 ml of toluene, and the mixture was stirred in a closed vessel at 65° C. for 5 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with in each case 25 ml of water. The combined organic phases were dried over sodium sulphate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel (ethyl acetate/heptane=20:80) gave 7.3 g (87% of theory) of the diastereomeric methyl 4-cyano-4-(3,4-difluorophenyl)-3-(3-fluorophenyl)butanoate (erythro:threo=65:35 according to integration of the methyl singlets in the 1H-NMR in CDCl3 at 3.68 and 3.59 ppm).
Aufarbeitung
- customThe solvent was removed under reduced pressure
- washthe mixture was washed twice with in each case 25 ml of water
- dry with materialThe combined organic phases were dried over sodium sulphate
- customthe solvent was removed under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-e8affb76ef4c4349879bc781c10d1e72
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09084425B2
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