Potassium Permanganate → HCID 17977726, compound

HRID 2254704Notes

Reaction equation

HRID 2254704 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[OH:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].[Mn]([O-])(=O)(=O)=O.[K+]>O>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:14]([O:15][CH3:16])[CH:13]=2)=[O:18])[CH:20]=1

Participants

5

Reactant 3

HCID 516875Potassium PermanganateHCID 5462222PotassiumHCID 13365804alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

Product 1

HCID 17977726HCID 17977726, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

ba) 3.2 g of alpha-[4-(benzyloxy)-5-methoxyphenyl]-3-pyridinemethanol suspended in 50 ml of water are treated with 2.5 g of potassium permananate, whereupon the mixture is stirred at 90° for 30 minutes After adding a further 1.0 g of potassium permanganate and stirring for a further 30 minutes at 90° the mixture is cooled to room temperature and extracted twice with 150 ml of ethyl acetate each time. The combined ethyl acetate phases are washed with sodium chloride solution, dried over sodium sulfate and evaporated. The thus-obtained residue is chromatographed on 50 g of silica gel with ethyl acetate. After recrystallization from methylene chloride/hexane there is obtained 4-(benzyloxy)-3-methoxyphenyl 3-pyridyl ketone of m.p. 76°.

Workup

  1. stirringstirring for a further 30 minutes at 90° the mixture
  2. extractionextracted twice with 150 ml of ethyl acetate each time
  3. washThe combined ethyl acetate phases are washed with sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe thus-obtained residue is chromatographed on 50 g of silica gel with ethyl acetate
  7. customAfter recrystallization from methylene chloride/hexane there

Sources & evidence

ORD record
ord-e7edc2016314459da541837ccb15e819
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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