Acetic Acid → Methyl pyrrole-2-carboxylate

HRID 397951Notes

Reaction equation

HRID 397951 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[N+](=[CH2:11])=[N-].C(O)(=O)C>C(OCC)C>[CH3:11][O:7][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 12473Pyrrole-2-Carboxylic Acid

Product 1

HCID 136930Methyl pyrrole-2-carboxylateYield 88.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Method 4 General Experimental: Pyrrole-2-carboxylic acid (90.0 mmol, 10.0 g) in diethyl ether (200 ml) was treated with diazomethane (270 mmol, generated from N-nitroso-N-methyl urea), then back titrated with acetic acid until the yellow color dissipated. The solution was washed with saturated aqueous sodium bicarbonate (3×20 ml) and brine (3×20 ml), then concentrated under reduced pressure to provide 10 g (88%) of pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) δ9.14 (1H, s), 6.98-6.65 (1H, m), 6.94-6.91 (1H, m), 6.29-6.26 (1H, m), 3.86 (3H, s).

Workup

  1. washThe solution was washed with saturated aqueous sodium bicarbonate (3×20 ml) and brine (3×20 ml)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6576346116e84844b4c73c7572967998
Source dataset
uspto-grants-2003_08
Patent number
US06610730B2

Reaction notes

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