Methyl iodide → ethyl 2,4-dimethyl-3-oxopentanoate

HRID 241000Notes

Reaction equation

HRID 241000 reaction equation
[CH3:1][CH:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI>C1COCC1>[CH3:12][CH:4]([C:3](=[O:10])[CH:2]([CH3:1])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 225905ethyl 2,4-dimethyl-3-oxopentanoateYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 4-methyl-3-oxopentanoate (3.0 g, 19.0 mmol) and potassium carbonate (7.86 g, 56.9 mmol) in THF (40 mL) was stirred at room temperature for 3 h under N2 (g). The mixture was cooled to 0° C. and methyl iodide (3.23 g, 22.8 mmol) was added dropwise over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 16 h. Subsequent filtration and concentration provided ethyl 2,4-dimethyl-3-oxopentanoate (2.89 g, 89% yield) as a clear yellow oil that was used without further purification. MS (EI) for C9H16O3: 172 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. filtrationSubsequent filtration and concentration

Sources & evidence

ORD record
ord-53d447776bcf4e558eb92c74c4d4bbaf
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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