Methanol → Methyl pyrrole-2-carboxylate

HRID 2291930Notes

Reaction equation

HRID 2291930 reaction equation
Cl[C:2]([C:4]1[NH:5][CH:6]=[CH:7][CH:8]=1)=[O:3].N1C=CC=CC=1.[CH3:15][OH:16]>C(Cl)Cl>[NH:5]1[CH:6]=[CH:7][CH:8]=[C:4]1[C:2]([O:16][CH3:15])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 224558Pyrrole-2-carbonyl chloride

Product 1

HCID 136930Methyl pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 ml of a solution of 45 (mmoles) of 2-chlorocarbonyl-1H-pyrrole in methylene chloride were added dropwise to a cold mixture of 4.3 ml of pyridine and 3.5 ml of methanol and the mixture was washed with water, then with 6 ml of N sodium hydroxide, and was extracted with methylene chloride. The organic phases were dried and concentrated to dryness and the residue was chromatographed over silica. Elution with a mixture of hexane and ethyl acetate (8-2) yielded 4.014 g of methyl 1H-pyrrole-2-carboxylate melting at ≈74° C.

Workup

  1. washthe mixture was washed with water
  2. extractionwith 6 ml of N sodium hydroxide, and was extracted with methylene chloride
  3. customThe organic phases were dried
  4. concentrationconcentrated to dryness
  5. customthe residue was chromatographed over silica
  6. washElution
  7. additionwith a mixture of hexane and ethyl acetate (8-2)

Sources & evidence

ORD record
ord-9a76a7893ea047259f364cf6c37542bd
Source dataset
uspto-grants-1989_01
Patent number
US04798901

Reaction notes

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