1-Chloro-4-nitrobenzene → 9-Decenal
Reaction equation
C1C([N+]([O-])=O)=CC=C(Cl)C=1.C([O:13][CH:14](OCC)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23])C.C(O)CCCCCCCC=C>>[CH:14](=[O:13])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-2bc30a429b044d2aa6f35d190598ca60
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06696597B2
Reaction notes
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