Water → Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 1285214Notes

Reaction equation

HRID 1285214 reaction equation
[CH3:1][NH2:2].[CH3:3][CH2:4][O:5][C:6]([CH2:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)=[O:7].Cl[CH2:18][C:19](=O)[CH3:20].O>C(Cl)Cl>[CH3:1][N:2]1[CH:18]=[C:19]([CH3:20])[C:8]([C:6]([O:5][CH2:4][CH3:3])=[O:7])=[C:9]1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 6571ChloroacetoneHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 118460Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetateYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

In a comparative example anhydrous gaseous methylamine was bubbled through a mixture of diethyl acetone dicarboxylate and chloroacetone in methylene chloride for about five minutes while the temperature rose from 25 to about 40° C. After reaction for one-half hour, water was added and the reaction mixture was heated to 90° C. for about one-half hour. Extraction with chloroform gave a dark oil containing 23 percent yield of desired ethyl 1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate.

Workup

  1. customrose from 25 to about 40° C
  2. customAfter reaction for one-half hour
  3. extractionExtraction with chloroform
  4. customgave a dark oil

Sources & evidence

ORD record
ord-e8ca12d1967543a9b21eaa462d8d8e1e
Source dataset
uspto-grants-1986_01
Patent number
US04565878

Reaction notes

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