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Synthesis of pinacolyl [ 14 C]methylphosphonochloridate
Author(s) -
Horvat J.,
Keglević D.,
Klaić B.,
Kveder S.,
Ladešić B.,
Ćosić M.,
Zupanc S.
Publication year - 1982
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.2580190609
Subject(s) - chemistry , thionyl chloride , methyl iodide , yield (engineering) , sodium iodide , iodide , alcohol , nuclear chemistry , medicinal chemistry , sodium , radiochemistry , chloride , organic chemistry , materials science , metallurgy
Abstract A three‐step synthetic route to pinacolyl [ 14 C] methylphosphonochloridate () from [ 14 C]methyl iodide is described Condensation of sodium di‐ n ‐butyl phosphite with [ 14 C] methyl iodide gave di‐ n ‐butyl [ 14 C] methylphosphonate () which was converted into [ 14 C] methylphosphonic dichloride () by prolonged refluxing with thionyl chloride. Reaction of with pinacolyl alcohol in the presence of N , N ‐di‐ n ‐propylaniline as the base afforded the title compound . The radiochemical yield of redistilled was 34.2% based on , and the overall radiochemical yield was 20.0% from [ 14 C] methyl iodide.