6-Methyl-5-hepten-2-one → 3,7-Nonadienoic acid, 4,8-dimethyl-, methyl ester

HRID 2164186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164186
[CH3:1]C(C)=CCCC(=O)C.[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([OH:16])=[O:15].[Cl-].[C:24]([CH2:27]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O>CS(C)=O>[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH3:1])=[O:15].[CH3:10][C:11]([CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:12][CH2:13][C:14]([O:16][CH2:24][CH3:27])=[O:15]

Komponenten

6

Edukt 3

HCID 98626-Methyl-5-hepten-2-oneHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 54343890HCID 54343890, Verbindung

Produkt 2

HCID 5497503,7-Nonadienoic acid, 4,8-dimethyl-, methyl esterHCID 53706627Ethyl 4,8-dimethylnona-3,7-dienoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

6-Methyl-5-hepten-2-one is converted into 4,8-dimethylnona-3,7-dienoic acid by reaction with β-carboxyethyltriphenylphosphonium chloride in dimethylsulfoxide using the method of H. S. Corey et al., J. Am. Chem. Soc. 86, 1884 (1964). The trans and cis isomer can be separated by chromatography at this point or a mixture of the two isomers employed in further reactions. The acid is then converted into the acid chloride using thionyl chloride at roomm temperature or slightly higher. The acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes to yield the ester, methyl 4,8-dimethylnona-3,7-dienoate and ethyl 4,8-dimethylnona-3,7-dienoate.

Aufarbeitung

  1. customThe trans and cis isomer can be separated by chromatography at this point
  2. additiona mixture of the two isomers
  3. additionThe acid chloride is then treated with an alcohol, such as methanol or ethanol, at a temperature of about 40° for a few minutes

Quellen und Nachweise

ORD-Eintrag
ord-f0581ef25f564578bbff1248f7c1f3af
Quelldatensatz
uspto-grants-1979_01
Patentnummer
US04137273

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