Reaktion #5762

Reaktionsgleichung

water

oxalic acid

2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

diisobutylaluminium hydride

→

2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

Ausbeute 84.0%

Lösungsmittel

n-hexane

n-hexane

n-hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   SonstigeResultant white precipitates
4. 4
   Filtrationwere filtered
5. 5
   Waschenwashed
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigeto give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   ExtraktionThe organic layer was extracted
10. 10
    Sonstigeseparated
11. 11
    Waschenwashed with water
12. 12
    Trocknendried over MgSO4
13. 13
    Einengenconcentrated

Vorschrift

To a solution of 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (856 mg, 3.0 mmol) in n-hexane (30 ml) was added a 0.5 M solution of diisobutylaluminium hydride in toluene (6 ml) with stirring at -70° C. under argon atmosphere. After one hour, water (3 ml) was added, the cooling bath was removed, and the reaction mixture was stirred well. Resultant white precipitates were filtered and washed. The filtrate was concentrated to give a residue, which was dissolved in n-hexane (10 ml). The n-hexane solution was combined with a 10% aqueous solution of oxalic acid (5 ml) and stirred for 3 hours. The organic layer was extracted and separated, washed with water, dried over MgSO4, and concentrated. The resultant residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=10:1) to obtain 2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (865 mg, 84%).

Quelle