Nitrogen → HCID 14508126, compound

Participants

Reaction Conditions

Reaction Steps

A 2000 ml flask, equipped with mechanical stirring, a condenser and N2 atmosphere, is charged with 24.3 g of N2 and 400 ml of ethanol to prepare sodium ethylate. After cooling to 15° C., the ethyl-2-acetyl-4-methyl-4-pentenoate (161.4 g) is added to the solution over 30 min while maintaining the temperature at 15° C.-20° C. To this is then added, all at once, 15 g of iodide. The exothermic reaction is controlled with an ice bath to keep the temperature at 30° C. for about 90 min. Stirring is continued over 2 hrs and 30 min at 20° C., and the mixture is then taken to reflux for 4 hrs. The reaction mixture is left at rest for 56 hrs, and then the NaI precipitate is filtered. Toluene (700 ml) is added and the mixture filtered again. Toluene/ethanol azeotrope (700 ml) (rotavapor. 74° C./6× 104Pa) is distilled and 250 ml of the distillate is added to the residue. After cooling to 5° C., a new filtration is carried out. The filtrate is evaporated (74° C./2.7×104Pa). Raw product is purified on a Vigreux column, and then in a glass bolos column topped by a total reflux head, to yield ethyl-2-acetyl-2,4-dimethyl-4-pentenoate.

Provenance & Evidence