✍ Scribed by Henri Hoellinger; Nguyen-Hoang Nam; Jean-François Decauchereux; Louis Pichat
No coin nor oath required. For personal study only.
Cross‐coupling of 3,5‐dimethoxybenzyl bromide and 4‐buten‐magnesium bromide in presence of Li~2~CuCl~4~ afforded 1‐(3,5‐dimethoxyphenyl)‐4pentene. Demethylation of the latter by methylmagnesium iodide in xylene gave rise to 4′,5′‐dehydro‐olivetol. The latter, condensed with trans‐p‐mentha‐2,8‐dien‐1‐ol in the presence of either boron trifluoride etherate or p‐toluenesulfonic acid, gave 4′,5′‐dehydro‐Δ^9^‐ and Δ^8^‐THC respectively. 4′,5′‐dehydro‐Δ^8^‐THC was also obtained by isomerization of 4′,5′‐dehydro‐Δ^9^‐THC. Catalytic selective reduction of these precursors with deuterium or tritium, in the presence of tris(triphenylphosphine)rhodium chloride, afforded Δ^9^‐THC‐4′,5′,‐^2^H or Δ^9^‐THC‐4′,5′‐^3^H (50 Ci/mMole) and Δ^8^‐THC‐4′,5′‐^2^H or Δ^8^‐THC‐4′,5′‐^3^H (56 Ci/mMole).
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