Pyrrole → HCID 136395931, compound

HRID 1488441Notes

Reaction equation

HRID 1488441 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]=O)[CH:8]=1)[CH3:2].[NH:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>C(O)(=O)CC>[CH2:1]([O:3][C:4]([CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[C:20]3[NH:16][C:17]([C:13]([C:9]4[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:8]=4)=[C:17]4[N:16]=[C:20]([C:13]([C:9]5[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:8]=5)=[C:17]5[NH:16][C:20](=[C:13]([C:9]6[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])[CH:8]=6)[C:17]6[CH:18]=[CH:19][C:20]=2[N:16]=6)[CH:19]=[CH:18]5)[CH:19]=[CH:18]4)=[CH:18][CH:19]=3)[CH:10]=[CH:11][CH:12]=1)=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 8027PyrroleHCID 15237912Ethyl 3-(3-formylphenyl)propanoate

Product 1

HCID 136395931HCID 136395931, compound

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
60 °C

Procedure

20.62 g (0.10 mol) of 3-{3-formylphenyl)-propionic acid ethyl ester (CARN 110114-05-1) is dissolved in 300 ml of propionic acid and the solution is heated to 60° C. 6.71 g (0.10 mol) of pyrrole is slowly instilled and the dark solution is stirred for 1 hour at 110° C. After cooling, it is completely concentrated by evaporation in a vacuum, the residue is taken up in dichloromethane and shaken out with saturated aqueous sodium bicarbonate solution. After the drying of the organic phase on sodium sulfate, it is filtered and concentrated by evaporation, and the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/ethanol. The residue of the product fractions that are concentrated by evaporation is recrystallized from isopropanol.

Workup

  1. temperatureAfter cooling
  2. concentrationit is completely concentrated by evaporation in a vacuum
  3. stirringshaken out with saturated aqueous sodium bicarbonate solution
  4. customAfter the drying of the organic phase on sodium sulfate, it
  5. filtrationis filtered
  6. concentrationconcentrated by evaporation
  7. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/ethanol
  8. concentrationThe residue of the product fractions that are concentrated by evaporation
  9. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-673b2e8747904d6bb4694d3a5a229468
Source dataset
uspto-grants-1997_10
Patent number
US05674467

Reaction notes

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