Ethanol → Ethyl 4-formyl-1H-pyrrole-2-carboxylate

HRID 44257Notes

Reaction equation

HRID 44257 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[NH:9][CH:8]=[C:7]([CH:10]=[O:11])[CH:6]=1)=[O:4].[CH2:14]([O-])[CH3:15].[Na+].C([OH:20])C>>[CH:10]([C:7]1[CH:6]=[C:5]([C:3]([O:4][CH2:14][CH3:15])=[O:20])[NH:9][CH:8]=1)=[O:11]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 2723922Sodium ethoxideHCID 124599775-Trichloroacetyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 321486Ethyl 4-formyl-1H-pyrrole-2-carboxylate

Procedure

To a solution of the compound obtained in Step B (83.7 mmoles) in ethanol (200 ml) there is added, dropwise and over 20 minutes, a solution of sodium ethanolate (13.4 mmoles) in ethanol (45 ml) at ambient temperature. After stirring for 3 hours, the mixture is evaporated to dryness and then taken up in ethyl ether (200 ml). To that organic phase there is added aqueous 2N HCl solution (150 ml) and the resulting mixture is stirred; the phases are then separated and the aqueous phase is extracted with ethyl ether. The organic phase is washed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness to yield the title product (brown crystals), which is used directly in the next Step.

Workup

  1. customat ambient temperature
  2. customthe mixture is evaporated to dryness
  3. additionTo that organic phase there is added aqueous 2N HCl solution (150 ml)
  4. stirringthe resulting mixture is stirred
  5. customthe phases are then separated
  6. extractionthe aqueous phase is extracted with ethyl ether
  7. washThe organic phase is washed with saturated aqueous NaHCO3 solution and with saturated aqueous NaCl solution
  8. dry with materialdried over sodium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-3adbc94614604f3d9fa09f3bb4fa267c
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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