Iodoethane → Ethyl 3-oxocyclopentanecarboxylate

HRID 424620Notes

Reaction equation

HRID 424620 reaction equation
[CH2:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][C:3](=[O:4])[CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:16](I)[CH3:17]>CN(C=O)C>[CH2:16]([O:8][C:7]([CH:6]1[CH2:1][CH2:2][C:3](=[O:4])[CH2:5]1)=[O:9])[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 2277983-Oxocyclopentanecarboxylic acid

Product 1

HCID 223136Ethyl 3-oxocyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of cyclopentanone-3-carboxylic acid (5.00 g, 39 mmol), caesium carbonate (12.82 g, 39 mmol) and ethyl iodide (9.12 g, 4.75 ml, 58.5 mmol) in DMF (50 ml) was stirred at RT for 18 h. The mixture was then concentrated i. vac., the residue was taken up in toluene, the mixture was concentrated again and 2 N hydrochloric acid and EtOAc were then added. The aq. phase was extracted with EtOAc (3×30 ml) and the combined organic phases were washed with aq. sodium thiosulfate soln. The organic phase was dried with Na2SO4 and concentrated i. vac.

Workup

  1. concentrationThe mixture was then concentrated i
  2. concentrationthe mixture was concentrated again
  3. addition2 N hydrochloric acid and EtOAc were then added
  4. extractionThe aq. phase was extracted with EtOAc (3×30 ml)
  5. washthe combined organic phases were washed with aq. sodium thiosulfate soln
  6. dry with materialThe organic phase was dried with Na2SO4
  7. concentrationconcentrated i

Sources & evidence

ORD record
ord-fc56e6ea41b8428494878975ccad468a
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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