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

HRID 2292839Notes

Reaction equation

HRID 2292839 reaction equation
[CH:1]([N:3]([CH2:5][C:6](O)=O)C)=O.[C:9]([O:13][CH2:14][CH3:15])(=[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][CH2:14][CH3:15])=[O:12])=[CH:11]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 12182Ethyl propiolateHCID 11789184N-formylsarcosine

Product 1

HCID 11062584Ethyl 1-methyl-1H-pyrrole-3-carboxylateYield 71.3%

Procedure

A mixture of 117.1 g (1 mole) of N-formylsarcosine prepared in the Reference Example 1, 98.10 g (1 mole) of ethyl propiolate, and 638 ml of acetic anhydride was stirred using a magnetic stirrer over an oil bath at 130° C. for 22 hours. The reaction mixture was concentrated under vacuum. 100 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 109.19 g (yield 71.3%) of a colorless or light-yellow oil of the title compound as fractions with a boiling point of 103°-104° C. at 4 mmHg.

Workup

  1. customat 130° C.
  2. customfor 22 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. addition100 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-2ebda8a98dc6462f80216314e767d8d3
Source dataset
uspto-grants-1997_11
Patent number
US05684161

Reaction notes

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