1-Chloro-4-nitrobenzene → 9-Decenal

Participants

Reaction Steps

FIG. 40 shows a synthesis of PNCB which involves the cross-metathesis of vinyl borate pinacol ester (Matheson, D. S J Am Chem Soc (1960) 82, 4228-4233) with 9-decenal diethyl acetal (synthesized by the Swern oxidation of commercially available 9-decenol to yield 9-decenal, then protecting it as the acetal with ethanol and hydrochloric acid) with Catalyst 823 to yield the pinacol ester of 1-borodecenal diethyl acetal. This product was coupled with Z-1-iodohexene (Normant Org Syn VII, p 290-294) under Suzuki conditions as described by Miycuira Org Syn VIII p 532, to yield E-9,Z-11-hexadecadienal diethyl acetal. This material was purified by column chromatography, and the acetal was hydrolyzed in aqueous methanol and water with cat p-toluenesulfonic acid at 35° C. for 24 hours. E-9,Z-11-hexadecadienal was isolated by concentrating the reaction mixture and purified by column chromatography.

Provenance & Evidence