Water → HCID 18668439, compound

HRID 1058533Notes

Reaction equation

HRID 1058533 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH:15]([CH2:24][CH3:25])[C:16]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH3:23])=[O:17].O>CN(C=O)C>[CH2:22]([O:21][CH2:20][CH2:19][O:18][C:16]([CH:15]([N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7])[CH2:24][CH3:25])=[O:17])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13854Pyrrole-2-carboxaldehydeHCID 18668436HCID 18668436, compound

Product 1

HCID 18668439HCID 18668439, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of pyrrole-2-carboxaldehyde (9.5 g, 0.1 mole), anhydrous potassium carbonate (27.6 g, 0.2 mole) and 2-ethoxyethyl α-bromobutyrate (23.6 g, 0.105), as previously described, were kept under stirring in 20 ml DMF at room temperature for 12 hours. The reaction mixture was carefully poured into water, extracted with ethylacetate and the extracts were dried on sodium sulfate. After evaporation of the solvent, 15.5 g of 1-[1-(2-ethoxyethoxycarbonyl)-propyl]-2-formyl pyrrole were obtained as a brown oil, which was used in the subsequent step without any further purification.

Workup

  1. extractionextracted with ethylacetate
  2. customthe extracts were dried on sodium sulfate
  3. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-cdc5aaf9c9d7453886c71684d1f8f8c2
Source dataset
uspto-grants-2003_02
Patent number
US06518005B2

Reaction notes

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