Sodium Hydroxide → Mcn 2891

HRID 1834401Notes

Reaction equation

HRID 1834401 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][C:9]=2[CH3:21])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118464ethyl 5-(4-chlorobenzoyl)-alpha,1,4-trimethyl-1H-pyrrole-2-acetate

Product 1

HCID 198126Mcn 2891

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution of 2.9 g. (0.0087 mole) of ethyl 5-(p-chlorobenzoyl)-1,4,α-trimethylpyrrole-2-acetate is added to 17.5 ml. 0.5 N sodium hydroxide solution and the mixture is heated under reflux for 1 hour. The ethanol is evaporated in vacuo and the solution poured into dilute hydrochloric acid. The precipitated solid is collected by filtration and recrystallized from ether-cyclohexane to give 5-(p-chlorobenzoyl)-1,4,α-trimethylpyrrole-2-acetic acid as a white solid, m.p. 153°-154° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe ethanol is evaporated in vacuo
  3. additionthe solution poured into dilute hydrochloric acid
  4. filtrationThe precipitated solid is collected by filtration
  5. customrecrystallized from ether-cyclohexane

Sources & evidence

ORD record
ord-e2f012da2aa74fbd8e50a955245cad74
Source dataset
uspto-grants-1978_01
Patent number
US04070368

Reaction notes

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