Réaction #696705

Équation de réaction

4-bromo-1-butene

Ethyl acetoacetate

sodium ethoxide

→

ethyl 2-acetyl-5-hexenoate

Rendement 91.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed for 5 hours
2. 2
   FiltrationThe resulting solution was filtered
3. 3
   workup.ADDITIONethyl acetate was added (75 ml)
4. 4
   Lavagewashed with a solution of hydrochloric acid (2×200 ml, 5N) and brine (100 ml)
5. 5
   SéchageThe organic layer was dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autresolvent removed under reduced pressure

Mode opératoire

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.

Source