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

HRID 330129Notes

Reaction equation

HRID 330129 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-fa4618c1db2242de93307074dfcf34db
Source dataset
uspto-grants-1990_01
Patent number
US04894464

Reaction notes

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