Potassium Permanganate → HCID 24786837, compound

HRID 1469663Notes

Reaction equation

HRID 1469663 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+].OS([O-])=O.[Na+]>CC(C)=O.CC(C)=O.O.Cl>[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([C:16]([OH:19])=[O:17])=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 71349636Benzyl 5-formyl-1H-pyrrole-2-carboxylate

Product 1

HCID 24786837HCID 24786837, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Next, to a stirred solution of 5-formyl-1H-pyrrole-2-carboxylic acid benzyl ester (1.10 g, 4.80 mmol) in acetone (100 mL) is added a solution of potassium permanganate (1.52 g, 9.60 mmol) in 150 mL acetone/water (1:1) dropwise and the mixture is stirred for three hours. The mixture is poured into a solution of 200 mL of 10% NaHSO3 in 1N HCl and the mixture is extracted three times with ethyl acetate. The combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound; HPLC Retention time 0.88 minutes (condition C): MS 244.3 (M−1).

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe combined organic layers are washed with water and brine
  3. dry with materialthen is dried over magnesium sulfate
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-96055b6fb683474d8853e12c6b7b5c9b
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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