Oxygen → Butanoic acid, 2-ethyl-3-oxo-, methyl ester

HRID 898509

Reaction equation

HRID 898509 reaction equation
O=O.[CH3:3][C:4](C)([O-])C.[K+].[C:9]([O:15][CH3:16])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].C(I)C>C1COCC1.O>[CH2:3]([CH:10]([C:11](=[O:12])[CH3:13])[C:9]([O:15][CH3:16])=[O:14])[CH3:4]

Participants

7

Reactant 4

HCID 977OxygenHCID 6340IodoethaneHCID 7757Methyl acetoacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 103534Butanoic acid, 2-ethyl-3-oxo-, methyl esterYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere free of water and oxygen, to a three-necked flask equipped with a dropping funnel were successively added 0.15 mol of potassium tert-butoxide and 150 ml of THF, then stirrer was started. 0.12 Mol of methyl acetoacetate was slowly dropped to the reactor cooled in an ice-water bath. Upon completion of the dropping, the reaction was continued at room temperature for further 1 hr. Then 0.18 mol of ethyl iodide was slowly dropped at room temperature, and then the reaction was heated to reflux for 6 hrs. At the end of the reaction, solvent was evaporated by using a rotatory evaporator, and saturated saline was added to just dissolve the solid. Organic phase was separated, and aqueous phase was extracted with a suitable amount of diethyl ether for three times. The combined organic phase was washed well with saturated saline, then dried over anhydrous sodium sulfate. Solvent was removed by using a rotatory evaporator, and the residue was distilled under reduced pressure to give 0.072 mol of product. Yield 60%.

Workup

  1. customstirrer was started
  2. temperaturecooled in an ice-water bath
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 6 hrs
  5. customAt the end of the reaction, solvent
  6. customwas evaporated
  7. customa rotatory evaporator, and saturated saline
  8. additionwas added
  9. dissolutionto just dissolve the solid
  10. customOrganic phase was separated
  11. extractionaqueous phase was extracted with a suitable amount of diethyl ether for three times
  12. washThe combined organic phase was washed well with saturated saline
  13. dry with materialdried over anhydrous sodium sulfate
  14. customSolvent was removed
  15. customa rotatory evaporator
  16. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-c84c755c67df4f19a3082ab714451149
Source dataset
uspto-grants-2008_04
Patent number
US07351778B2

Linked notes

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