Reaktion #44925

Reaktionsgleichung

sodium chloride

acetophenone

ethyl diethylphosphonoacetate

sodium hydride

→

product

Ausbeute 128.9%

ethyl (E)-3-phenylbut-2-enoate

Ausbeute 128.9%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture is extracted with ether
2. 2
   TrocknenThe organic phase is dried (Na2SO4)
3. 3
   Sonstigethe solvents are evaporated off under reduced pressure

Vorschrift

A mixture of 10 g (0.25 mol) of sodium hydride and tetrahydrofuran is heated to 50° C., followed by dropwise addition over 30 minutes of a solution of 48 ml (0.19 mol) of ethyl diethylphosphonoacetate in 80 ml of tetrahydrofuran. A solution of 28.4 g (0.24 mol) of acetophenone in 60 ml of tetrahydrofuran is added dropwise at 0° C. and the mixture is stirred for 16 hours at 25° C. 250 ml of saturated sodium chloride solution are added at 0° C. and the resulting mixture is extracted with ether. The organic phase is dried (Na2SO4) and the solvents are evaporated off under reduced pressure. The 46.6 g of product obtained are purified by flash chromatography (90/10 cyclohexane/diisopropyl ether) (29 g; 63%).

Quelle