Reaction #696705

Reaction equation

4-bromo-1-butene

Ethyl acetoacetate

sodium ethoxide

→

ethyl 2-acetyl-5-hexenoate

Yield 91.0%

Solvents

ethanol

Conditions

Workup

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

Procedure

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