Iodoethane → 4-(1-Cyano-1-ethylpropyl)benzonitrile
Reaktionsgleichung
[C:1]([CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)#[N:2].[CH2:12](I)[CH3:13].[H-].[Na+].[CH3:17][CH2:18]OC(C)=O>CCCCCCC.O.CN(C=O)C>[C:1]([C:3]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)([CH2:12][CH3:13])[CH2:17][CH3:18])#[N:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4-Cyanomethylbenzonitrile (1.02 g, 7.18 mmol) and ethyl iodide (2.25 g, 14.4 mmol) are added to DMF (20.0 mL), and the resulting solution is cooled to 0° C. NaH (576 mg, 14.4 mmol) is added in portions. The mixture is warmed to room temperature and then stirred for 3 hours. Water (100 mL) is added, and the aqueous phase is extracted with EtOAc (4 times with 50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by Combi-Flash silica gel chromatography, eluting with mixtures of heptane and EtOAc (100/0 to 70/30), (936 mg, 5.51 mmol, 77%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.42 Hz, 6H) 1.89-2.14 (m, 4H) 7.64 (d, J=8.40 Hz, 2H) 7.92 (d, J=8.59 Hz, 2H).
Aufarbeitung
- temperatureThe mixture is warmed to room temperature
- extractionthe aqueous phase is extracted with EtOAc (4 times with 50.0 mL)
- dry with materialThe combined organic phases are dried with MgSO4
- filtrationfiltered
- concentrationconcentrated on the rotovaporator
- customThe product is purified by Combi-Flash silica gel chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-10ba435c4cd842f48206c1b80667c273
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08093402B2
Notizen zur Reaktion
Wird geladen…