Trimethylsulfonium iodide → 2-(Pyrid-3-yl)-4-methylbutane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

20 g (0.134 mol) of 3-pyridyl isopropyl ketone and 30.2 g (0.268 mol) of potassium tert-butylate were dissolved in 200 ml of tert-butanol. Thereafter, 37.4 g (0.208 mol) of trimethylsulfonium iodide were added and the mixture was heated at 65° C. for 1.5 hours. The inorganic salts were separated off and the reaction solution was evaporated down, after which 75 ml of half-concentrated H2SO4 were added to the crude product and the mixture was heated at 60°-70° C. for 8 hours. The pH was then brought to 9 with 4N NaOH solution and extraction was carried out with methylene chloride. The organic phase was dried and evaporated down and the product was then purified by chromatography.

Provenance & Evidence