Acetic Acid → Methyl pyrrole-2-carboxylate

HRID 1057752Notes

Reaction equation

HRID 1057752 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

Pyrrole-2-carboxylic acid (10.0 g, 90.0 mmol) 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), followed by brine (3×20 mL), then was evaporated to obtain 10 g (88%) of product. 1H NMR (CDCl3) δ 3.86 (s, 3H), 6.26-6.29 (m, 1H), 6.91-6.94 (m, 1H), 6.65-6.98 (m, 1H), 9.14 (s, 1H).

Workup

  1. washThe solution was washed with saturated aqueous sodium bicarbonate (3×20 mL)
  2. customwas evaporated

Sources & evidence

ORD record
ord-268acb65b0c6421b8b5a879040aef447
Source dataset
uspto-grants-2003_02
Patent number
US06514997B2

Reaction notes

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