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Synthesis of [5‐ 14 C]‐dodecane and [8‐ 14 C]‐hexadecane
Author(s) -
Schenk Torsten,
Schmidt Burkhard
Publication year - 1993
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.2580330912
Subject(s) - chemistry , dodecane , hexadecane , yield (engineering) , bromide , wittig reaction , lithium (medication) , alkyl , organic chemistry , sulfonate , carboxylic acid , medicinal chemistry , sodium , medicine , materials science , metallurgy , endocrinology
[5‐ 14 C]‐Dodecane and [8‐ 14 C]‐Hexadecane were synthesized starting with [1‐ 14 C]‐octanoic acid. The carboxylic acid was reduced to 1‐octanol, which was esterified to n‐octyl p‐toluenesulfonate. Following a Corey‐House procedure, the sulfonate was either reacted with Li[Cu(butyl) 2 ] to [5‐ 14 C]‐dodecane (40 % overall yield), or with Li[Cu(octyl) 2 ] to [8‐ 14 C]‐hexhadecane (24 % overall yield). The lithium di‐alkyl cuprates were prepared from butyl lithium and n‐octyl bromide, respectively. Preliminary experiments with non‐labeled compounds using a wittig reaction as chain extension step, turned out to be less favourable. The Corey‐House route provides a simple method for the synthesis of specifically 14 C‐labeled alkanes from commercially available [1‐ 14 C]‐carboxylic acids.