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Synthesis of nona‐deutero olivetol and nona‐deutero cannabinoids
Author(s) -
Seltzman Herbert H.,
Begum Mosammat K.,
Wyrick Christopher D.
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580290905
Subject(s) - chemistry , alkyl , grignard reagent , bromide , grignard reaction , reagent , medicinal chemistry , chemical synthesis , stereochemistry , coupling (piping) , organic chemistry , in vitro , biochemistry , mechanical engineering , engineering
Copper (I) catalyzed Grignard cross coupling of alkyl bromides provided a facile synthesis of d 9 ‐olivetol [5‐(2,2,3,3,4,4,5,5,5‐ 2 H 9 )pentyl‐1,3‐benzenediol] with high d 9 incorporation levels and no detectable levels of d 0 to d 7 ions. The outcome of the coupling is dependent on which bromide is used as the Grignard reagent. d 9 ‐Δ 9 ‐THC and racemic d 9 ‐11‐hydroxy‐Δ 9 ‐THC suitable for GC/MS analysis were prepared from the olivetol.