Reacción #696705

Ecuación de reacción

4-bromo-1-butene

Ethyl acetoacetate

sodium ethoxide

→

ethyl 2-acetyl-5-hexenoate

Rendimiento 91.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was refluxed for 5 hours
2. 2
   FiltraciónThe resulting solution was filtered
3. 3
   workup.ADDITIONethyl acetate was added (75 ml)
4. 4
   Lavadowashed with a solution of hydrochloric acid (2×200 ml, 5N) and brine (100 ml)
5. 5
   SecadoThe organic layer was dried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otrosolvent removed under reduced pressure

Procedimiento

Ethyl acetoacetate (6.57 g, 0.05 mol) was dissolved in ethanol (25 ml) and sodium ethoxide (3.9 g, 0.55 mol) was added. The solution was cooled to room temperature and 4-bromo-1-butene (6.96 g, 0.05 mole) was added. The mixture was refluxed for 5 hours. The resulting solution was filtered, ethyl acetate was added (75 ml), and washed with a solution of hydrochloric acid (2×200 ml, 5N) and brine (100 ml). The organic layer was dried (MgSO4), filtered, and solvent removed under reduced pressure to give ethyl 2-acetyl-5-hexenoate in the form of a light yellow liquid (9.29 g) in 91% yield.

Fuente