Reaktion #340395

Reaktionsgleichung

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

ethyl propanoate

sodium ethoxide

→

2-[3,4-bis(methyloxy)phenyl]-3-oxopentanenitrile

Ausbeute 30.9%

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 saturated 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 (2.0 g, 11 mmol) and ethyl propanoate (1.61 mL, 14 mmol) in ethanol (4 mL) was added a sodium ethoxide solution (21%, 8.4 mL, 23 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 saturated sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give 2-[3,4-bis(methyloxy)phenyl]-3-oxopentanenitrile as a brown oil (0.8 g, 3.4 mmol, 30% yield), MS (EI) for C13H15NO3: 234 (MH+).

Quelle