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Synthesis of 4‐hydroxy[4‐ 3 H]‐2(E)‐nonen‐1‐al‐diethylacetal
Author(s) -
Bravais Fabienne,
Rao Dinesh,
Alary Jacques,
Rao Renée C.,
Debrauwer Laurent,
Bories Georges
Publication year - 1995
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.2580360511
Subject(s) - chemistry , yield (engineering) , hexanal , medicinal chemistry , swern oxidation , organic chemistry , materials science , metallurgy , dimethyl sulfoxide
4‐Hydroxy‐2(E)‐nonen‐1‐al‐diethylacetal 3 (HNE‐DEA) was prepared by condensation of the Grignard compound derived from propiolaldehyde diethylacetal and n‐hexanal followed by reduction of the resulting 4‐hydroxy‐2‐nonyn‐1‐al‐diethylacetal 2 with LiAlH 4 according to the literature procedure with minor modifications. Swern oxidation [DMSO + (COCl 2 )] of 3 gave 30% yield of 4‐oxo‐2(E)‐nonen‐1‐al‐diethylacetal 5 . [ 3 H]NaBH 4 and [ 2 H]NaBH 4 reduction of 5 gave rise respectively to [4‐ 3 H]HNE‐DEA (specific activity 222 GBq/mmol) and [4‐ 2 H]HNE‐DEA.