Reaktion #606846

Reaktionsgleichung

hydrochloric acid

sodium hydride

ethyl 3-oxohexanoate

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

→

title compound

Ausbeute 101.9%

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

Ausbeute 101.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 16 hr
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe obtained ethyl acetate layer was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a suspension (200 mL) of 60% sodium hydride (1.8 g) in tetrahydrofuran was added dropwise a solution (50 mL) of ethyl 3-oxohexanoate (10.9 g) in tetrahydrofuran at 0° C. The mixture was stirred at the same temperature for 30 min, 4′-(bromomethyl)-2′-fluorobiphenyl-2-carbonitrile (10.0 g) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into 1 N hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow oil (12.9 g, 100%).

Quelle