Dichloromethane → Methyl pyrrole-2-carboxylate

HRID 1703311Notes

Reaction equation

HRID 1703311 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

  1. customThe solution was evaporated to dryness in vacuo
  2. additionthe resulting acid chloride converted to ester by addition of 30 ml
  3. additionEther (50 ml.) was added
  4. extractionthe mixture extracted with 50 ml
  5. dry with materialThe ether phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-faedd2132e694639b78fe250504c12ce
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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