Sodium Hydroxide → 5-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

HRID 1457450Notes

Reaction equation

HRID 1457450 reaction equation
[CH2:1]([C:8]1[NH:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([C:8]1[NH:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14449694HCID 14449694, compound

Product 1

HCID 184690125-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130°-134° C.; 1H NMR(CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 h
  3. customThe major part of the ethanol was removed
  4. additionthe remaining liquid was diluted with water
  5. washwashed with ether
  6. temperaturecooled in ice
  7. extractionThe mixture was extracted with ether
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto afford 0.567 g (92%) of an off white solid

Sources & evidence

ORD record
ord-cead61097b514bf6ae7dc2bdc90be888
Source dataset
uspto-grants-1998_12
Patent number
US05847135

Reaction notes

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