Ammonium Chloride → HCID 15661752, compound

Participants

Reaction Conditions

Reaction Steps

A solution of octylmagnesium bromide (produced from 150 mg of magnesium in 5 ml of diethyl ether and 1.14 g of octyl bromide in 2.5 ml of diethyl ether) is instilled in a solution of 1.17 g of 5-(6-bromo-2-pyridyl)-(E,E)-2,4-pentadienaldehyde in 25 ml of diethyl ether with stirring and under argon atmosphere at -20° C. After 1.5 hours at -20° C., the reaction mixture is mixed with 15 ml of saturated ammonium chloride solution, shaken out with diethyl ether, dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate=95/5. 477 mg of 2-bromo-6-[(1E,3E)-(5RS)-5-hydroxy-1,3-tridecadienyl]-pyridine is obtained as crude product.

Provenance & Evidence