HCID 86744246, compound → HCID 14884231, compound

HRID 1087790Notes

Reaction equation

HRID 1087790 reaction equation
[CH:1]1([N:8]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17]CC)=[O:16])=[CH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[OH-].[Na+]>[CH:1]1([N:8]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86744246HCID 86744246, compound

Product 1

HCID 14884231HCID 14884231, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 38 g of the ester in 400 ml ethanol and 200 ml of 1.5N aqueous sodium hydroxide is stirred at room temperature for 16 hours. The ethanol is evaporated at 50° and reduced pressure and the basic solution is washed with ethyl acetate, made acidic with ice cold 5N aqueous hydrochloric acid and extracted into ethyl acetate; the extract is washed with brine, dried over MgSO4, treated with charcoal and filtered. The solvent is evaporated at 50° and reduced pressure and the residue is crystallized from ether to yield (E)-3-(1-cycloheptyl-1H-pyrrol-3-yl)-2-propenoic acid, m.p. 138°-140°.

Workup

  1. customThe ethanol is evaporated at 50°
  2. washreduced pressure and the basic solution is washed with ethyl acetate
  3. extractionextracted into ethyl acetate
  4. washthe extract is washed with brine
  5. dry with materialdried over MgSO4
  6. additiontreated with charcoal
  7. filtrationfiltered
  8. customThe solvent is evaporated at 50°
  9. customreduced pressure and the residue is crystallized from ether

Sources & evidence

ORD record
ord-d9c2004f1957423cb9efddffafbea64f
Source dataset
uspto-grants-1990_10
Patent number
US04960787

Reaction notes

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