Sodium Hydroxide → HCID 12897042, compound

HRID 1980905Notes

Reaction equation

HRID 1980905 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([O:16]C)=[O:15])[CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[NH:13][CH:12]=[C:11]([C:14]([OH:16])=[O:15])[CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12897050HCID 12897050, compound

Product 1

HCID 12897042HCID 12897042, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 5-(4-fluorophenylthio)pyrrole-3-carboxylate (1.5 g.) was combined with 10 ml. of methanol and 10 ml. of 1N sodium hydroxide and refluxed for 2 hours. The methanol was allowed to evaporate, the aqueous residue was diluted with approximately one volume of water and extracted twice with ether. The aqueous phase was cooled in an ice-water bath and acidified to pH 2.0 with conc. hydrochloric acid. The gummy solid which precipitated was extracted into ethyl acetate. The three combined ethyl acetate extracts were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Trituration with hexane gave crystalline 5-(4-fluorophenylthio)pyrrole-3-carboxylic acid (1.17 g., m.p. 116-118, m/e 237), recovered by filtration.

Workup

  1. customto evaporate
  2. additionthe aqueous residue was diluted with approximately one volume of water
  3. extractionextracted twice with ether
  4. temperatureThe aqueous phase was cooled in an ice-water bath
  5. customThe gummy solid which precipitated
  6. extractionwas extracted into ethyl acetate
  7. washThe three combined ethyl acetate extracts were washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated to an oil

Sources & evidence

ORD record
ord-b87b6821b1cf4b079ea640806d8a72b0
Source dataset
uspto-grants-1985_04
Patent number
US04511575

Reaction notes

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