Water → 5-(Ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole-3-propanoic Acid Methyl Ester

HRID 1860934Notes

Reaction equation

HRID 1860934 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:18])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2].O.[N+]([O-])([O-])=[O:21].[NH4+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH:18]=[O:21])=[C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 22985Ammonium nitrateHCID 291754Ethyl 4-(3-methoxy-3-oxopropyl)-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 155335575-(Ethoxycarbonyl)-2-formyl-4-methyl-1H-pyrrole-3-propanoic Acid Methyl EsterYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethyl-4-(2-methoxycarbonylethyl)-1H-pyrrole-2-carboxylic acid ethyl ester (127 g) was dissolved in acetic acid (1900 mL), water (1900 mL) and tetrahydrofuran (1900 mL) and cooled to −30° C. Cerric ammonium nitrate (1097 g) was added in portions with stirring to give a reddish-orange suspension. The suspension was stirred at 0° C. for 2 hours, neutralized to pH 7 with sodium bicarbonate and extracted with ethyl acetate (2000 mL). The ethyl acetate layer was separated, washed with brine (200 mL) and dried over anhydrous sodium sulfate (20 g). The solvent was removed to give 80.2 g (60%) of 5-formyl-4-(2-methoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as an oil.

Workup

  1. customto give a reddish-orange suspension
  2. stirringThe suspension was stirred at 0° C. for 2 hours
  3. extractionextracted with ethyl acetate (2000 mL)
  4. customThe ethyl acetate layer was separated
  5. washwashed with brine (200 mL)
  6. dry with materialdried over anhydrous sodium sulfate (20 g)
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-c747722d4175452a9d702528a9edf3db
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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