1-Pentene → 8-Dodecen-1-ol, (8Z)-

HRID 879040

Reaktionsgleichung

Reaktionsgleichung von HRID 879040
[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].[CH2:11]=[CH:12][CH2:13]CC>C1COCC1>[CH2:1]([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:11][CH2:12][CH3:13]

Komponenten

4

Edukt 2

HCID 80041-PenteneHCID 11094728Non-8-en-1-ol

Produkt 1

HCID 52832958-Dodecen-1-ol, (8Z)-Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a glovebox, a 20 mL vial was charged with 8-nonenol (0.58 g, 4.1 mmol), 1-pentene (4 mL), and THF (4 mL). A solution of 1 (0.026 g, 1 mol %) in THF (0.5 mL) was added, and the mixture was stirred in an open vial for 4 hours. The vial was removed from the glovebox, the reaction was quenched with excess ethyl vinyl ether, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, using a gradient of hexanes to 20% EtOAc in hexanes) provided 12 (0.56 g, 73% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.36 (2H, m), 3.64 (2H, br t, J=5.3 Hz), 2.01 (4H, m), 1.36 (2H, m), 1.28-1.40 (11H, m), 0.90 (3H, t, J=7.4 Hz); 13C NMR (CDCl3): δ 130.0, 129.7, 63.1, 32.8, 29.3 (4C), 27.2, 25.7, 22.9, 13.8; HRMS (EI): 184.1805, [C12H24O]+ requires 184.1827.

Aufarbeitung

  1. customThe vial was removed from the glovebox
  2. customthe reaction was quenched with excess ethyl vinyl ether
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3a71b7006f57472caad31a2fb3821c47
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987531B2

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