Sodium Hydroxide → HCID 20464742, compound

HRID 325431Notes

Reaction equation

HRID 325431 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:4]=[C:3]1[CH:21]=[O:22].[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[CH:4]=[C:3]1[CH:21]=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20464723HCID 20464723, compound

Product 1

HCID 20464742HCID 20464742, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A sample of ethyl 1-methyl-2-formyl-4-(3-methylphenoxymethyl)pyrrole-5-carboxylate (3.24 g, 10 mmol) is dissolved in hot ethanol (50 ml) and 10% aqueous NaOH is added (10 ml). The resulting mixture is heated at reflux until all starting material has been consumed. The solution is cooled, diluted with water (140 ml) and acidified to pH 2 with 6 N HCl. The resulting two-phase mixture is extracted with ethyl acetate (2×100 ml). The combined ethyl acetate layers are then washed with saturated brine (50 ml), and dried over sodium sulfate. The solvent is removed to give a residue which crystallizes on standing. This material is sufficiently pure for use in the next step.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux until all starting material
  3. customhas been consumed
  4. temperatureThe solution is cooled
  5. additiondiluted with water (140 ml)
  6. extractionThe resulting two-phase mixture is extracted with ethyl acetate (2×100 ml)
  7. washThe combined ethyl acetate layers are then washed with saturated brine (50 ml)
  8. dry with materialdried over sodium sulfate
  9. customThe solvent is removed
  10. customto give a residue which
  11. customcrystallizes

Sources & evidence

ORD record
ord-d18a79c58feb417eb25d5e794c0844b3
Source dataset
uspto-grants-1984_04
Patent number
US04440779

Reaction notes

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