Ethyl Acetoacetate → Ethyl 2-acetyl-6-methyl-5-heptenoate

HRID 743910Notes

Reaction equation

HRID 743910 reaction equation
[H-].[Na+].[C:3]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].Br[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17]>C1COCC1>[C:5]([CH:4]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:3]([O:9][CH2:10][CH3:11])=[O:8])(=[O:6])[CH3:7]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 1375215-Bromo-2-methyl-2-pentene

Product 1

HCID 12705511Ethyl 2-acetyl-6-methyl-5-heptenoateYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride was added portionwise to a stirred solution of ethyl acetoacetate (0.1 mole, 13.0 g) in 300 ml THF. The solution was stirred for 30 minutes. 5-Bromo-2-methyl-2-pentene (0.11 moles, 17.9 g) was added dropwise over 30 minutes. The solution stirred at room temperature for 40 hours. The solution was concentrated in vacuo. Ethyl acetate and water were added. The organic phase was dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with a gradient of 0-40% ethyl acetate in hexane to yield 4.5 g of ethyl 2-acetyl-6-methyl-5-heptenoate.

Workup

  1. stirringThe solution stirred at room temperature for 40 hours
  2. concentrationThe solution was concentrated in vacuo
  3. additionEthyl acetate and water were added
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product was purified by HPLC over silica gel
  7. washeluted with a gradient of 0-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-50a207fd3b374a0795f8665e988692ad
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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