Synthesis of Nona-Deuteroolivetol and Nona-Deutero Cannabinoids
Copper (I) catalyzed Grignard cross coupling of alkyl bromides provided a facile synthesis of d9‐olivetol [5‐(2,2,3,3,4,4,5,5,5‐2H9)pentyl‐1,3‐benzenediol] with high d9 incorporation levels and no detectable levels of d0 to d7 ions. The outcome of the coupling is dependent on which bromide is used as the Grignard reagent. d9‐Δ9‐THC and racemic d9‐11‐hydroxy‐Δ9‐THC suitable for GC/MS analysis were prepared from the olivetol.
Seltzman, H., Begum, M., & Wyrick, C. (1991). Synthesis of Nona-Deuteroolivetol and Nona-Deutero Cannabinoids. Journal of Labelled Compounds and Radiopharmaceuticals, 29(9), 1009-1018. https://doi.org/10.1002/jlcr.2580290905