Ethanol → HCID 15766626, compound

HRID 2253799Notes

Reaction equation

HRID 2253799 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([O:15][CH3:16])[C:13](C(OCC)=O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.[CH2:22]([OH:24])C>O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([O:15][CH3:16])[CH:13]=[C:12]([C:22]([OH:24])=[O:1])[CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 20084727HCID 20084727, compound

Product 1

HCID 15766626HCID 15766626, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Sodium hydroxide (50%, 2.75 g, 0.0343 mol) in water is added to a stirred solution of ethyl 5-(p-chlorophenyl)-1-methoxypyrrole-2-carboxylate (8.0 g, 0.0286 mol) in ethanol. The reaction mixture is heated at reflux temperature for 2 hours, cooled to room temperature, diluted with water and extracted with ether. The aqueous layer is acidified with 10% hydrochloric acid and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to yield a solid which upon trituration with boiling hexanes gives the title compound as a white crystalline solid (7.0 g, 97%), m.p. 189°-191° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature for 2 hours
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. washThe combined ether extracts are washed sequentially with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto yield a solid which upon trituration with boiling hexanes

Sources & evidence

ORD record
ord-aedcf78171584d4c8a9ec6404627524b
Source dataset
uspto-grants-1993_08
Patent number
US05232979

Reaction notes

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