Potassium Hydroxide → Ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionate

HRID 971874Notes

Reaction equation

HRID 971874 reaction equation
[OH-].[K+].[C:3]([CH:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1>CN(C)C=O>[CH2:6]([O:5][C:3]([C:8]1([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[CH2:12][CH2:11][CH2:10][C:9]1=[O:13])=[O:4])[CH3:7]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 10998728Ethyl 2-[4-(chloromethyl)phenyl]propanoate

Product 1

HCID 11131780Ethyl 2-[4-(1-ethoxycarbonyl-2-oxocyclopentan-1-ylmethyl)phenyl]propionateYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 200 ml of dimethyl formamide containing 6.0 g of potassium hydroxide was added 15.6 g of 2-carboethoxycyclopentanone with stirring at room temperature to give a homogeneous solution. Under ice-cooling, 25 g of ethyl 2-(p-chloromethylphenyl)propionate was added dropwise thereto, and the mixture was heated at 80° C. with stirring for 2 hours. After completion of the reaction, the reaction mixture was poured into an ice-water, extracted with ether, the extract washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 28 g of an oily substance, which was subjected to a vacuum distillation affording 21 g of the desired compound, b.p. 175°-178° C. at 0.5 mm Hg.

Workup

  1. customto give a homogeneous solution
  2. temperatureUnder ice-cooling
  3. temperaturethe mixture was heated at 80° C.
  4. stirringwith stirring for 2 hours
  5. customAfter completion of the reaction
  6. extractionextracted with ether
  7. washthe extract washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent removed by distillation
  10. customto give 28 g of an oily substance, which
  11. distillationwas subjected to a vacuum distillation

Sources & evidence

ORD record
ord-98fee958f28c4e25b26ca7ceca45c8a0
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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