Reaktion #607061

Reaktionsgleichung

hydrochloric acid

sodium hydride

ethyl 3-oxohexanoate

4′-(bromomethyl)-2′-nitrobiphenyl-2-carbonitrile

→

title compound

Ausbeute 82.0%

ethyl 2-[(2′-cyano-2-nitrobiphenyl-4-yl)methyl]-3-oxohexanoate

Ausbeute 82.0%

Lösungsmittel

—

oil

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature overnight
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe ethyl acetate layer was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

To a mixture of 60% sodium hydride in oil (0.85 g) and tetrahydrofuran (20 mL) was added dropwise a mixture of ethyl 3-oxohexanoate (4.50 g) in tetrahydrofuran (10 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. Then, the aforementioned 4′-(bromomethyl)-2′-nitrobiphenyl-2-carbonitrile was added, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 M hydrochloric acid (30 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a yellow oil (4.60 g, 82%).

Quelle