Methyl acetoacetate → 4-Pentenoic acid, 2-acetyl-, methyl ester

HRID 1107125Notes

Reaction equation

HRID 1107125 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH2:9](Br)[CH:10]=[CH2:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:4]=[C:3]([CH3:5])[CH:2]([CH2:11][CH:10]=[CH2:9])[C:1]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 1071874-Pentenoic acid, 2-acetyl-, methyl esterYield 56.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl acetoacetate (11.6 g, 100 mmol), allyl bromide (12.1 g, 100 mmol) and potassium carbonate (13.8 g, 100 mmol) in acetone (70 mL) is heated under reflux for 18 hours. The mixture is filtered and the filtrate is evaporated. The residue is chromatographed on silica gel (15:1 hexane:ethyl acetate) to give methyl 3-oxo-2-(1-propen-3-yl)butanoate (8.8 g, 47%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 2.22 (s, 3H), 2.58 (t, 2H), 3.54 (t, 1H), 3.72 (s, 3H), 4.90-5.12(m, 2H), 5.60-5.82 (m, 1H).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 hours
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated
  5. customThe residue is chromatographed on silica gel (15:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-c9624d4ebfd240fe86838d4acc58b5e1
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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