Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:14]=[C:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][C:21](OC)=[O:22].[O-]CC.[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([C:21](=[O:22])[CH2:20][N:16]2[CH2:17][CH2:18][CH2:19][C:15]2=[O:14])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]Komponenten
Versuchsvorschrift
To a mixture of [3,4-bis(methyloxy)phenyl]acetonitrile (1.0 g, 5.5 mmol) and methyl (2-oxopyrrolidin-1-yl)acetate (1.0 g, 7.0 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 4.2 mL, 11 mmol), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, it was poured into a mixture of ice-water (50 mL). This aqueous mixture was washed with dichloromethane (3×20 mL) then acidified to pH 1. The acidified mixture was extracted with ethyl acetate (3×30 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give 2-[3,4-bis(methyloxy)phenyl]-3-oxo-4-(2-oxopyrrolidin-1-yl)butanenitrile as a brown oil (0.43 g, 1.4 mmol, 25% yield), MS (EI) for C16H18N2O4: 303 (MH+).
Aufarbeitung
- temperaturethe resulting mixture was heated
- temperatureat reflux for 18 hours
- washThis aqueous mixture was washed with dichloromethane (3×20 mL)
- extractionThe acidified mixture was extracted with ethyl acetate (3×30 mL)
- extractionThe combined extract
- washwas washed with aqueous sodium bicarbonate solution, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-808e0f393b3a4a628f7f087ed182a181
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07872014B2
Verknüpfte Notizen
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