Diethyl Ether → 5-Decen-1-ol, (5E)-

HRID 2122095

Reaktionsgleichung

Reaktionsgleichung von HRID 2122095
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CC[O:8][CH2:9][CH3:10]>[Cl-].[Zn+2].[Cl-]>[CH2:9]([OH:8])[CH2:10][CH2:4][CH2:3]/[CH:2]=[CH:1]/[CH2:1][CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 178418339Butyllithium

Produkt 1

HCID 52832925-Decen-1-ol, (5E)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

FIG. 16 shows a synthesis of 5-decenyl acetate which involves the cross-metathesis of vinyl borate pinacol ester (Matheson, D. S J Am Chem Soc (1960) 82, 4228-4233) with 5-hexenol THP ether (or 1,10-diTHP ether of 5-decene) with Catalyst 823 to yield a pinacol ester of 1-borohexen-6-ol THP ether. This product was coupled with butyl lithium and zinc chloride under Suzuki conditions as described by Miycuira (Org Syn VIII p 532) to yield E-5-decenol THP ether in a 91:9 E:Z isomeric ratio. This material was purified by column chromatography and then acetated to yield 5-decenyl acetate in 91:9 E:Z isomeric ratio.

Quellen und Nachweise

ORD-Eintrag
ord-6629ec883f154be9845d35421b4dfbaf
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696597B2

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