Ethyl Acetoacetate → Ethyl 2-acetyl-5-hexenoate

HRID 609523Notes

Reaction equation

HRID 609523 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[O-]CC.[Na+].Br[CH2:15][CH2:16][CH:17]=[CH2:18]>C(O)C>[C:3]([CH:2]([CH2:18][CH2:17][CH:16]=[CH2:15])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 21241Homoallyl bromideHCID 2723922Sodium ethoxide

Product 1

HCID 5214007Ethyl 2-acetyl-5-hexenoateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. filtrationThe resulting solution was filtered
  3. additionethyl acetate was added (75 ml)
  4. washwashed with a solution of hydrochloric acid (2×200 ml, 5N) and brine (100 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-14454523c287473b8277380d7c818cea
Source dataset
uspto-grants-1999_12
Patent number
US05998092

Reaction notes

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