Methanol → methyl 2-(2-methoxy-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylate

Reaction equation

[C:1]([CH2:4][C:5]1[N:6]([CH3:13])[CH:7]=[CH:8][C:9]=1[C:10](O)=[O:11])([OH:3])=[O:2].[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:25][OH:26]>>[CH3:25][O:26][C:10]([C:9]1[CH:8]=[CH:7][N:6]([CH3:13])[C:5]=1[CH2:4][C:1]([O:3][CH3:14])=[O:2])=[O:11]

Participants

Reactant 3

HCID 887Methanol

HCID 6101p-Toluenesulfonic acid

HCID 30194323-Carboxy-1-methyl-1H-pyrrole-2-acetic acid

Product 1

HCID 44475349methyl 2-(2-methoxy-2-oxoethyl)-1-methyl-1H-pyrrole-3-carboxylate

Procedure

2-Carboxymethyl-1-methyl-1H-pyrrole-3-carboxylic acid (17.67 g) prepared as described by Bottaccio, Giorgio; Campolmi, Stefano; Carletti, Vittorio; Marchi, Marcello. EP105664, para-toluenesulfonic acid (9.17 g) and methanol (250 ml) were refluxed under argon for 48 hours. The solvent was evaporated and the residue washed with ethanol to yield the title compound as a white solid (15.75 g)