1-Methylpyrrole → 1H-Pyrrole-2-acetic acid, 1-methyl-, ethyl ester

HRID 2163614Notes

Reaction equation

HRID 2163614 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 73041-MethylpyrroleHCID 12192Ethyl diazoacetate2×

Product 1

HCID 974691H-Pyrrole-2-acetic acid, 1-methyl-, ethyl ester

Procedure

In a flask is placed 9.72 grams (120 mmol) N-methyl pyrrole and 158 mg (.016 mmole; 1.5 mol%) Cu(acetylacetonate)2, abbreviated herein as "Cu(acac)2 ". The mixture is heated to 50° C. after which a few drops of the 4.56 grams (40 mmol) ethyl diazoacetate are added with stirring. Nitrogen gas is evolved after about 1 minute and the mixture darkens, whereupon the remainder of the ethyl diazoacetate is added drop by drop over a period of 15 minutes. The reaction mixture is then heated and stirred for a further 45 minutes to insure completion of the reaction.

Workup

  1. customIn a flask is placed
  2. additionare added
  3. temperatureThe reaction mixture is then heated
  4. stirringstirred for a further 45 minutes
  5. customcompletion of the reaction

Sources & evidence

ORD record
ord-814032cba9bb4d948921b588aab54068
Source dataset
uspto-grants-1979_01
Patent number
US04136097

Reaction notes

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