Ethanol → Ethyl 1-ethyl-2-oxocyclopentane-1-carboxylate

HRID 434752Notes

Reaction equation

HRID 434752 reaction equation
[Na].[CH2:2](O)[CH3:3].[C:5]([CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])([O:7][CH2:8][CH3:9])=[O:6].C(I)C>[Cl-].[Na+].O.O>[CH2:2]([C:10]1([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:14][CH2:13][CH2:12][C:11]1=[O:15])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 5360545Sodium

Product 1

HCID 10607544Ethyl 1-ethyl-2-oxocyclopentane-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In a three-necked flask 5.0 g. of sodium metal was dissolved in 250 ml. of dry ethanol and 31.24 g. (0.20 mole) 2-carboethoxycyclopentanone added. To the resulting yellow solution 18.4 ml. (0.23 mole) ethyl iodide was added dropwise and the mixture heated at reflux for two hours. After cooling, 250 ml. of brine and 50 ml. of water were added and the mixture extracted with ethyl ether (2×100 ml.). After drying (MgSO4) and evaporation of solvent 36.5 g. (99%) of 2-ethyl-2-carboethoxycyclopentanone was obtained.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for two hours
  3. temperatureAfter cooling
  4. extractionthe mixture extracted with ethyl ether (2×100 ml.)
  5. customAfter drying
  6. custom(MgSO4) and evaporation of solvent 36.5 g

Sources & evidence

ORD record
ord-0e652e5ad49c4a29ac4c0572bec891bf
Source dataset
uspto-grants-1983_08
Patent number
US04399163

Reaction notes

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