Potassium Hydroxide → 1H-Pyrrole, 3-(phenylmethyl)-

HRID 1156495Notes

Reaction equation

HRID 1156495 reaction equation
[C:1]([C:9]1[CH:10]=[C:11](C(OC)=O)[NH:12][CH:13]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O.NN>C(O)COCCOCCO>[CH2:1]([C:9]1[CH:10]=[CH:11][NH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2764013Methyl 4-benzoyl-1H-pyrrole-2-carboxylate

Product 1

HCID 117688281H-Pyrrole, 3-(phenylmethyl)-Yield 71.2%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

12.0 g (52.4 mmole) of methyl 4-benzoyl-2-pyrrolecarboxylate, 8.79 g (157 mmole) of potassium hydroxide and 10.5 g (210 mmole) of hydrazine hydrate are dissolved in 150 ml of triethylene glycol. Reaction is carried out by stirring the solution at 120° C. for 2 hours and then at 160° C. for 3 hours in the an atmosphere of nitrogen gas. After reaction is finished, the reaction solution is allowed to cool and poured into ice water, followed by extraction with ether. The extract is washed with water saturated with sodium chloride and concentrated. The residue is distilled under reduced pressure to obtain 5.86 g of 3-benzylpyrrole as a colorless liquid. Yield 71.2%. nD29.5 1.5790. Boiling point 95°-98° C. (0.09 mmHg).

Workup

  1. customReaction
  2. waitat 160° C. for 3 hours in the an atmosphere of nitrogen gas
  3. customAfter reaction
  4. temperatureto cool
  5. extractionfollowed by extraction with ether
  6. washThe extract is washed with water saturated with sodium chloride
  7. concentrationconcentrated
  8. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-cd5eaf82df5545a6a7a410f4be75f15c
Source dataset
uspto-grants-1982_06
Patent number
US04336194

Reaction notes

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