Methyl Acrylate → methyl 1H-pyrrole-3-carboxylate

HRID 1980963Notes

Reaction equation

HRID 1980963 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH:4]=[CH2:5].S(C[N+:20]#[C-:21])(C1C=CC(C)=CC=1)(=O)=O.O1CCC[CH2:23]1>O>[NH:20]1[CH:21]=[CH:23][C:4]([C:3]([O:7][CH3:8])=[O:6])=[CH:5]1

Participants

6

Reactant 4

HCID 7294Methyl AcrylateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanide

Product 1

HCID 12361759methyl 1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (57% dispersion in oil, 10.5 g., 0.25 mole) was placed in a flame dried flask and washed twice with dry benzene. Dry tetrahydrofuran (400 ml.) was added to the flask and the resulting slurry stirred under nitrogen. A mixture of methyl acrylate (11.3 ml., 0.128 moles) and tosylmethyl isocyanide (25 g., 0.128 moles) in 120 ml. of tetrahydrofuran was then added dropwise over 30 minutes. The reaction was exothermic and the reaction mixture refluxed during this process. After stirring for an additional hour (without external heating), the reaction mixture was cooled in an ice-water bath and water (approx. 120 ml.) added dropwise until solution resulted. The solution was allowed to warm and then extracted three times with ether. The combined ether extracts were back-washed with water and then saturated brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to yield methyl pyrrole-3-carboxylate (6.4 g., m.p. 78°-81° C., m/e 125).

Workup

  1. customdried flask
  2. washwashed twice with dry benzene
  3. additionDry tetrahydrofuran (400 ml.) was added to the flask
  4. temperaturethe reaction mixture refluxed during this process
  5. stirringAfter stirring for an additional hour
  6. temperature(without external heating)
  7. temperaturethe reaction mixture was cooled in an ice-water bath
  8. customresulted
  9. temperatureto warm
  10. extractionextracted three times with ether
  11. washThe combined ether extracts were back-washed with water
  12. dry with materialsaturated brine, dried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-c7a952d512984716a4bd73a6e7390370
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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