Reaktion #340403

Reaktionsgleichung

[3,4-bis(methyloxy)phenyl]acetonitrile

methyl (2-oxopyrrolidin-1-yl)acetate

sodium ethoxide

→

2-[3,4-bis(methyloxy)phenyl]-3-oxo-4-(2-oxopyrrolidin-1-yl)butanenitrile

Ausbeute 25.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture was heated
2. 2
   Temperaturat reflux for 18 hours
3. 3
   WaschenThis aqueous mixture was washed with dichloromethane (3×20 mL)
4. 4
   ExtraktionThe acidified mixture was extracted with ethyl acetate (3×30 mL)
5. 5
   ExtraktionThe combined extract
6. 6
   Waschenwas washed with aqueous sodium bicarbonate solution, brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

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+).

Quelle