(+-)-alpha-Pinene → (E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1yl)-2-buten-1-ol

Reaktionsgleichung

[CH3:1]/[C:2](=[CH:5]\[CH2:6][C@@H:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])/[CH:3]=[O:4].CC1C2C(C)(C)C(C2)CC=1>>[CH3:1]/[C:2](=[CH:5]\[CH2:6][C@@H:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])/[CH2:3][OH:4]

Komponenten

Edukt 2

HCID 6654(+-)-alpha-Pinene

HCID 15330881(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al

Produkt 1

HCID 15330882(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1yl)-2-buten-1-olAusbeute 80 %

Versuchsvorschrift

(E)-(S)-2-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)-2-buten-1-al synthesized from 1R,5R)-α-pinene having an optical purity of 97% e.e. (available from Aldrich) was hydrogenated in the same manner as in Example 1 to obtain 3.08 g (yield 80%) of the title compound. The chemical purity of the product was found to be 98% by GC.

Quellen und Nachweise

ORD-Eintrag: ord-72619ff7788740d3a5dcc669a8794d4e
Quelldatensatz: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06084138

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