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Synthesis of 6‐(10‐hydroxy‐[1‐ 14 C]decyl) ‐2,3‐dimethoxy‐5‐methyl‐1,4‐benzoquinone
Author(s) -
Hayashi Nobuyoshi,
Kato Shinji
Publication year - 1985
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.2580221009
Subject(s) - chemistry , yield (engineering) , benzoquinone , medicinal chemistry , hydrogen chloride , condensation , hydrogen , chloride , organic chemistry , materials science , physics , metallurgy , thermodynamics
6‐(10‐Hydroxy‐[1‐ 14 C]decyl)‐2,3‐dimethoxy‐5‐methyl‐1,4‐ benzoquinone (VIII) having a specific activity of 23.4 mCi/mmol was synthesized. 9‐(2‐Hydroxy‐3,4‐dimethoxy‐6‐methyl‐[carbonyl‐ 14 C] benzoyl)nonanol (VI) was obtained from the condensation of 3,4,5‐trimethoxytoluene with 10‐acetoxy‐[1‐ 14 C]decanoyl chloride (V) prepared from K 14 CN (I). Reduction of VI with hydrogen in the presence of Pd‐Cprovided 10‐(2‐hydroxy‐3,4‐dimethoxy‐6‐methylphenyl)‐[1‐ 14 C]decanol (VII). VII was oxidized with a Fremy's salt to give VIII in 21.5% radiochemical yield. 6‐(10‐Hydroxy‐decyl)‐2‐methoxy‐3‐[ 14 C]methoxy‐5‐methyl‐1,4‐ benzoquinone (XI) was prepared in 34.6% radiochemical yield from the reaction of [ 14 C]dimethyl sulfate with 6‐(10‐hydroxydecyl) ‐3‐hydroxy‐2‐methoxy‐5‐methyl‐1,4‐benzoquinone.