Реакция #696705

Уравнение реакции

4-bromo-1-butene

Ethyl acetoacetate

sodium ethoxide

→

ethyl 2-acetyl-5-hexenoate

Выход 91.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was refluxed for 5 hours
2. 2
   ФильтрацияThe resulting solution was filtered
3. 3
   workup.ADDITIONethyl acetate was added (75 ml)
4. 4
   Промывкаwashed with a solution of hydrochloric acid (2×200 ml, 5N) and brine (100 ml)
5. 5
   СушкаThe organic layer was dried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеsolvent removed under reduced pressure

Методика

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.

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