Synthesis of 4‐hydroxy[4‐³H]‐2(E)‐nonen‐1‐al‐diethylacetal

Abstract

Abstract 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.