Potassium Permanganate → HCID 59608115, compound

HRID 1469665Notes

Reaction equation

HRID 1469665 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:5][CH:4]=1)=[O:2].[Mn]([O-])(=O)(=O)=[O:20].[K+].OS([O-])=O.[Na+]>CC(C)=O.CC(C)=O.O.Cl>[CH2:12]([O:11][C:9]([C:6]1[N:7]([CH3:8])[C:3]([C:1]([OH:20])=[O:2])=[CH:4][CH:5]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 516875Potassium PermanganateHCID 12459981HCID 12459981, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 59608115HCID 59608115, compound

Reagents, catalysts & solvents 3

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

Procedure

Next, to a stirred solution of benzyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate (400 mg, 1.64 mmol) in acetone (25 mL) is added a solution of potassium permanganate (520 mg, 3.29 mmol) in 40 mL acetone/water (1:1) dropwise and the mixture is stirred for 3 hours. The mixture is poured into a solution of 60 mL 10% NaHSO3 in 1N HCl and the mixture is extracted with ethyl acetate (3×). 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 1.10 minutes (condition C); MS 260.3 (M+H).

Workup

  1. extractionthe mixture is extracted with ethyl acetate (3×)
  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-11d4968d8fc94676ad4be09c99a6df14
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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