Potassium Hydroxide → HCID 59576369, compound

HRID 2069511Notes

Reaction equation

HRID 2069511 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[CH:8]=[C:9]([CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C(O)C.O>[CH:12]1([CH2:11][C:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])[CH:8]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59576363HCID 59576363, compound

Product 1

HCID 59576369HCID 59576369, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Cyclopentylmethyl-1-(2,4-difluorobenzyl)-1H-pyrrole-2-carboxylic acid ethyl ester (A1-III) was taken in ethanol. To it a solution of potassium hydroxide in water was added and the reaction was refluxed for 18 hrs. Ethanol was evaporated; residue was diluted with water and washed with diethyl ether. The aqueous layer was acidified using dilute HCl and extracted with ethyl acetate. Ethyl acetate layer was washed with brine and dried over anhydrous sodium sulfate. Solvent was evaporated to get 4-cyclopentylmethyl-1-(2,4-difluorobenzyl)-1H-pyrrole-2-carboxylic acid (A1-IV).

Workup

  1. temperaturethe reaction was refluxed for 18 hrs
  2. customEthanol was evaporated
  3. additionresidue was diluted with water
  4. washwashed with diethyl ether
  5. extractionextracted with ethyl acetate
  6. washEthyl acetate layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customSolvent was evaporated

Sources & evidence

ORD record
ord-4ded272aae84492b99d3325a89dcfb79
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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