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

✍ Scribed by Fabienne Bravais; Dinesh Rao; Jacques Alary; Renée C. Rao; Laurent Debrauwer; Georges Bories

• Book ID: 102371204
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: French
• Weight: 278 KB
• Volume: 36
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580360511

✦ Synopsis

b) 50, Allbe de Las Planes, 31770 Colomiers (France) SUMMARY 4-Hydroxy-2(E)-nonen-1 -al-diethylacetal 9 (HNE-DEA) was prepared by condensation of the Grignard compound derived from propiolaldehyde diethylacetal and nhexanal followed by reduction of the resulting 4-hydroxy-2-nonyn-1-al-diethylacetal 2 with LiAIH4 according to the literature procedure with minor modifications. Swern oxidation [DMSO + (COCl2)] of 9 gave 30% yield of 4-oxo-Z(E)-nonen-l -al-diethylacetal 5.

[3H]NaBH4 and I2H]NaBH4 reduction of 5. gave rise respectively to (4-3H]HNE-DEA (specific activity 222 GBq/mrnol) and [4-*H]HNE-DEA.