Dichloromethane → Methyl pyrrole-2-carboxylate
Reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].S(Cl)(Cl)=O.[CH2:13](Cl)Cl>>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:13])=[O:7]Participants
4
Procedure
Pyrrole-2-carboxylic acid (5 g.) was combined with 200 ml. of methylene chloride and 20 ml. of thionyl chloride and refluxed for 2 hours. The solution was evaporated to dryness in vacuo and the resulting acid chloride converted to ester by addition of 30 ml. of methanol and 20 minutes stirring at room temperature. Ether (50 ml.) was added and the mixture extracted with 50 ml. of water. The ether phase was dried over anhydrous sodium sulfate, filtered and evaporated to yield methyl pyrrole-2-carboxylate (5 g., m.p. 69°-71° C.).
Workup
- customThe solution was evaporated to dryness in vacuo
- additionthe resulting acid chloride converted to ester by addition of 30 ml
- additionEther (50 ml.) was added
- extractionthe mixture extracted with 50 ml
- dry with materialThe ether phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-493e3043c7034a6fa92fc2f20529deaa
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04511576
Reaction notes
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