2-Methyl-5-vinylpyridine → 6-Methyl-3-pyridinecarboxaldehyde

HRID 637915Notes

Reaction equation

HRID 637915 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=C)=[CH:10][N:9]=1>O.COCCOC.[Os](=O)(=O)(=O)=O>[CH3:7][C:8]1[N:9]=[CH:10][C:11]([CH:14]=[O:2])=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 88172-Methyl-5-vinylpyridineHCID 23667635Sodium periodate

Product 1

HCID 101925666-Methyl-3-pyridinecarboxaldehydeYield 87%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

80 g (0.37 mole) of sodium periodate in 200 ml of water are added dropwise with vigorous stirring to 23 g (0.19 mole) of 2-methyl-5-vinyl pyridine in 800 ml of ethylene glycol dimethyl ether. 1.0 g (0.04 mole) of osmium tetroxide is then added while cooling with a mixture of ice and common salt, after which the mixture is stirred for 8 hours at room temperature in a nitrogen atmosphere. The oil remaining after removal of the solvent by evaporation in vacuo is taken up in a little water and extracted three times with ethyl acetate. Drying of the organic phase over sodium sulfate and concentration by evaporation in vacuo leave 20 g (87%) of a light brown oil which is immediately further processed.

Workup

  1. temperaturewhile cooling with a mixture of ice and common salt
  2. customafter removal of the solvent
  3. customby evaporation in vacuo
  4. extractionextracted three times with ethyl acetate
  5. dry with materialDrying of the organic phase over sodium sulfate and concentration by evaporation in vacuo

Sources & evidence

ORD record
ord-4d2a4bbd7ce244348f7121077d0b9e24
Source dataset
uspto-grants-1985_12
Patent number
US04559344

Reaction notes

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