Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([OH:9])=[O:8].[H-].[Na+].O.[CH3:13]N(C)C=O>>[CH3:13][O:8][C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:9]Participants
Procedure
The starting material is prepared as follows: The solution of 28 g of 1-methylpyrrole-2-carboxylic acid in 20 ml of dimethylformamide is added to the suspension prepared from 12 g of 50% sodium hydride in mineral oil, washed with petroleum ether and suspended in 50 ml of dimethylformamide, while stirring and cooling. Thereupon 30 ml of methyl iodide are added and stirring is continued at ambient temperature. Another 10 ml of methyl iodide are added after the initial exothermic reaction has subsided. After standing overnight, the mixture is treated with water, extracted with diethyl ether, the extract washed with aqueous sodium carbonate and water, dried and evaporated, to yield the 1-methylpyrrole-2-carboxylic acid methyl ester as an oil.
Workup
- customThe starting material is prepared
- washwashed with petroleum ether
- temperaturecooling
- additionThereupon 30 ml of methyl iodide are added
- stirringstirring
- customis continued at ambient temperature
- additionAnother 10 ml of methyl iodide are added after the initial
- customexothermic reaction
- extractionextracted with diethyl ether
- washthe extract washed with aqueous sodium carbonate and water
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-327e6677693244048f46825f908227e6
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256759
Linked notes
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