Dichloromethane → Methyl pyrrole-2-carboxylate

HRID 894079Notes

Reaction equation

HRID 894079 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

Reactant 3

HCID 6344DichloromethaneHCID 12473Pyrrole-2-Carboxylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 136930Methyl pyrrole-2-carboxylate

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-d82ba3a5c8ad44209ccd73b0771acca5
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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