Acetic Anhydride → Methyl 1-methyl-1H-pyrrole-3-carboxylate

HRID 2292841Notes

Reaction equation

HRID 2292841 reaction equation
[CH:1]([N:3]([CH2:5][C:6](O)=O)C)=O.[C:9]([O:13][CH3:14])(=[O:12])[C:10]#[CH:11].C(OC(=O)C)(=O)C>>[CH3:1][N:3]1[CH:5]=[CH:6][C:10]([C:9]([O:13][CH3:14])=[O:12])=[CH:11]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 13536Methyl propiolateHCID 11789184N-formylsarcosine

Product 1

HCID 22737888Methyl 1-methyl-1H-pyrrole-3-carboxylateYield 79.6%

Procedure

A mixture of 9.52 g (0.0813 mole) of N-formylsarcosine prepared in the Reference Example 1, 25.56 g (0.304 mole) of methyl propiolate, and 65 ml of acetic anhydride was stirred using a magnetic stirrer over an oil bath at 130° C. for 24 hours. The reaction mixture was concentrated under vacuum. 30 ml of toluene was added to the residue and the mixture was evaporated under reduced pressure. This procedure was repeated to obtain a brown oily substance. This oily substance was distilled under vacuum to obtain 9.01 g (yield 79.6%) of a colorless or light-yellow oil of the title compound as fractions with a boiling point of 93°-96° C. at 4 mmHg.

Workup

  1. customat 130° C.
  2. customfor 24 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. addition30 ml of toluene was added to the residue
  5. customthe mixture was evaporated under reduced pressure
  6. customto obtain a brown oily substance
  7. distillationThis oily substance was distilled under vacuum

Sources & evidence

ORD record
ord-85d3db5db56d4f62b10c5fe752498a5e
Source dataset
uspto-grants-1997_11
Patent number
US05684161

Reaction notes

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