Hydrochloric Acid → HCID 67319956, compound

HRID 339723Notes

Reaction equation

HRID 339723 reaction equation
Br[C:2]1[C:3]([C:15]([O:17]CC)=[O:16])=[C:4]([CH3:14])[N:5]([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:20][O-:21].[Na+].Cl>CO.[Cu]I>[CH3:20][O:21][C:2]1[C:3]([C:15]([OH:17])=[O:16])=[C:4]([CH3:14])[N:5]([CH3:13])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 15110858HCID 15110858, compound

Product 1

HCID 67319956HCID 67319956, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Procedure

The mixture of the 4-bromo-1,2-dimethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (2.91 g, 9.91 mmol), NaOMe (11.3 mL, 25% wt in MeOH) and CuI (566 mg, 2.97 mmol) in MeOH (35 mL) was refluxed overnight. The reaction mixture was poured into 1M HCl solution (100 mL) and extracted with ethyl acetate (200 mL). The organic phase was dried over MgSO4 and evaporated under vacuum to provide the title compound (2.56 g, 10.4 mmol, 105%).

Workup

  1. temperaturewas refluxed overnight
  2. extractionextracted with ethyl acetate (200 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-8831565cf91a43439588b2bde95d8cd6
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Reaction notes

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