Reaktion #95465

Reaktionsgleichung

quinoline

2,5-undecadiyn-1-ol

hydrogen

→

(Z,Z)-2,5-undecadien-1-ol

Ausbeute 69.6%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solution was filtered
2. 2
   Sonstigethe solvent was evaporated
3. 3
   Sonstigeto give 1.5 g of crude product which
4. 4
   Sonstigewas then purified by column chromatography on silica gel (50 g)
5. 5
   WaschenElution with ether-petroleum ether (1:4 parts by volume)

Vorschrift

2,5-undecadiyn-1-ol (1.5 g) in absolute ethanol (15 ml) was reduced with Lindlar catalyst (0.33 g) in the presence of quinoline (0.1 ml) at 25° C., 1 atm., for 7 h. The uptake of hydrogen stopped at 420 ml (theoretical 428 ml). The solution was filtered, and the solvent was evaporated to give 1.5 g of crude product which was then purified by column chromatography on silica gel (50 g). Elution with ether-petroleum ether (1:4 parts by volume) gave 1.07 g of (Z,Z)-2,5-undecadien-1-ol as an oil.

Quelle