Iodoethane → HCID 12586400, compound

HRID 132766Notes

Reaction equation

HRID 132766 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:17](I)[CH3:18]>CC(C)=O>[CH2:17]([C:3]1([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH3:18]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 12586400HCID 12586400, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under vigorously agitation, 14.8 g of methyl 2-oxocyclopentane carboxylate was added to 41.9 g of fine powdery anhydrous potassium carbonate, and after stirring for several minutes, to the mixture was added 100 ml of acetone. The reaction mixture was further stirred for 15 to 30 minutes at room temperature, then thereto was dropwise added 31.2 g of ethyl iodide. Upon the completion of the addition, the reaction mixture was heated for reflux for 2 hours. The solvent was removed under reduced pressure, and solid residue was washed with diethyl ether. The washing liquor was collected and washed with water. After removing the solvent, 18.0 g of pale yellow liquid was obtained, The liquid was distilled under reduced pressure, and 15.9 g of colorless liquid as a distillate cut of 122-124° C./25 mmHg was collected. Yield: 93.5%.

Workup

  1. stirringThe reaction mixture was further stirred for 15 to 30 minutes at room temperature
  2. additionUpon the completion of the addition
  3. temperaturethe reaction mixture was heated
  4. temperaturefor reflux for 2 hours
  5. customThe solvent was removed under reduced pressure, and solid residue
  6. washwas washed with diethyl ether
  7. customThe washing liquor was collected
  8. washwashed with water
  9. customAfter removing the solvent

Sources & evidence

ORD record
ord-4a68fffe941849c191da0e1b2fae572d
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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