RAPID ISOMERIZATION OF ALKYNOL BY POTASSIUM AMINOPROPYLAMIDE REAGENT

Hendig Winarno (Center for the Application of Isotopes and Radiation Technology, BATAN, Jakarta Jl. Cinere Pasar Jumat, Lebak Bulus, Jakarta 12440)

Indonesian Journal of Chemistry
Vol 7, No 3 (2007)

Terminal alkynol (w-alkynol) is an intermediate compound in synthesis of a potent anticancer agent, namely C-16 alkynic fatty acid. For synthesis of this intermediate compound, it is needed to synthesize the appropriate internal alkynol, namely 2-nonyn-1-ol (10), 2-undecyn-1-ol (11), and 2-heptyn-1-ol (12), subsequently to convert these internal alkynol into terminal alkynol, namely 8-nonyn-1-ol (7), 10-undecyn-1-ol (8), and 6-heptyn-1-ol (9), an isomerization reaction was needed. Based on the method which developed by ABRAMS by using potassium 3-aminopropylamide (KAPA) reagent, the isomerization reaction could be done within 5 minutes in 93-94% yield.