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

HRID 1262985Notes

Reaction equation

HRID 1262985 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-385f1661117b43c49cbaa672ecffc06b
Source dataset
uspto-grants-1984_06
Patent number
US04454328

Reaction notes

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