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

Participants

Reaction Steps

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.

Provenance & Evidence