Reaktion #1828949

Reaktionsgleichung

hydrogen

sodium hydride

diphenyl acetonitrile

Ethyl 3-chloropropionate

→

4-carbethoxy-2,2-diphenylbutanenitrile

Ausbeute 37.5%

Lösungsmittel

dimethylformamide

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeit was partitioned between water and ether
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Sonstigedried
4. 4
   SonstigeConcentration of the solvents afforded a residue which
5. 5
   workup.DISTILLATIONdistilled

Vorschrift

To a stirred suspension of sodium hydride (27 g of a 60% oil suspension) in 600 mL of dry dimethylformamide at room temperature was added over 1 hour a solution of diphenyl acetonitrile (130 g, o.67 mol) in 400 mL of DMF. the mixture was stirred until the evolution of hydrogen ceased, about 1 hour. Ethyl 3-chloropropionate (90 mL, 1 mol) was added dropwise over 1 hour and the resulting mixture was stirred for a further 1 hour, then it was partitioned between water and ether. The organic layer was washed with brine and dried. Concentration of the solvents afforded a residue which was vacuum distilled to give 4-carbethoxy-2,2-diphenylbutanenitrile (110 g).

Quelle