Potassium Iodide → Methyl 2-acetylhexanoate

HRID 890696Notes

Reaction equation

HRID 890696 reaction equation
[CH3:1][O:2][C:3](=[O:8])/[CH:4]=[C:5](/[O-:7])\[CH3:6].[Na+].[I-].[K+].[CH2:12](Br)[CH2:13][CH2:14][CH3:15]>CN1CCCN(C)C1=O>[C:5]([CH:4]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([O:2][CH3:1])=[O:8])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8002Butyl bromideHCID 23681258sodium (2E)-4-methoxy4-oxo-2-buten-2-olate

Product 1

HCID 12527573Methyl 2-acetylhexanoate

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
80 °C

Procedure

30 g (217 mmol) of sodium (2E)-4-methoxy-4-oxo-2-buten-2-olate (Example 13A) suspended in 1,3-dimethyltetrahydro-2(1H)-pyrimidone and 1.24 g (7.5 mmol) of potassium iodide are treated dropwise with 29.8 g (217 mmol) of butyl bromide and the mixture is stirred at 80° C. for 1 h under reflux. The cooled mixture is then added to ice water and extracted with diethyl ether. The ether phase is washed with sodium thiosulphate solution, dried, concentrated and chromatographed. The eluent used is cyclohexane having an increasing ethyl acetate content.

Workup

  1. temperatureunder reflux
  2. extractionextracted with diethyl ether
  3. washThe ether phase is washed with sodium thiosulphate solution
  4. customdried
  5. concentrationconcentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-d000757376de4d02a6ce64ed2ce04c11
Source dataset
uspto-grants-2006_02
Patent number
US06998402B2

Reaction notes

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