Hydrochloric Acid → 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic Acid

HRID 2120258Notes

Reaction equation

HRID 2120258 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH:14]=[O:15])=[C:5]([CH3:13])[C:6]=1[CH2:7][CH2:8][C:9]([O:11]C)=[O:10].Cl>[OH-].[Na+]>[C:9]([CH2:8][CH2:7][C:6]1[C:5]([CH3:13])=[C:4]([CH:14]=[O:15])[NH:3][C:2]=1[CH3:1])([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10536383Methyl 3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoate

Product 1

HCID 15125203-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)propanoic AcidYield 106%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2,4-Dimethyl-5-formyl-3-(2-methoxycarbonylethyl)pyrrole (0.23 g, 1.2 mmol) in 6N sodium hydroxide (10 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled to room temperature, acidified with 6 N hydrochloric acid and extracted three times with 10 mL of ethyl acetate. The combined organic layers were washed with 10 mL of water and 5 mL of brine, dried over anhydrous sodium sulfate and evaporated to dryness to give 230 mg (106% yield) of crude 4-carboxyethyl-3,5-dimethyl-2-formylpyrrole as a brown oil.

Workup

  1. extractionextracted three times with 10 mL of ethyl acetate
  2. washThe combined organic layers were washed with 10 mL of water and 5 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-29fe06a33b534f508acd8b186207d3d1
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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