Pyridine → Ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate

HRID 67110Notes

Reaction equation

HRID 67110 reaction equation
N1C=CC=CC=1.[C:7](Cl)([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8].[C:15]([O:18][CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1)(=[O:17])[CH3:16]>ClCCl>[C:15]([O:18][CH2:19][CH2:20][N:21]1[CH:22]=[CH:23][CH:24]=[C:25]1[C:7](=[O:8])[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 12674764HCID 12674764, compound

Product 1

HCID 12795013Ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxalate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In the next step, a solution of pyridine in anhydrous dichloromethane is added to a stirred and cooled solution of ethoxalyl chloride in anhydrous dichloromethane so that the reaction temperature remains at about -20° to -25° C. Upon completion of this addition an approximately equimolar amount of 1-(2-acetoxyethyl)pyrrole of Formula (III) in anhydrous dichloromethane is added while the temperature is maintained at temperatures of about 0° to -20° C. Washing with water, drying, removal of the solvent and purification gives ethyl 1-(2-acetoxyethyl)pyrrole-2-glyoxylate.

Workup

  1. customremains at about -20° to -25° C
  2. additionis added while the temperature
  3. temperatureis maintained at temperatures of about 0° to -20° C
  4. washWashing with water
  5. customdrying
  6. customremoval of the solvent and purification

Sources & evidence

ORD record
ord-ec5a8ef743984bf294e6074f301440ea
Source dataset
uspto-grants-1982_08
Patent number
US04344943

Reaction notes

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