Reaktion #5760

Reaktionsgleichung

water

2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitril

diisobutylaluminium hydride

→

2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienal

Ausbeute 90.0%

Lösungsmittel

n-hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   Sonstigefollowed by removal of the cooling bath and vigorous stirring
3. 3
   SonstigeThe resultant while precipitates
4. 4
   Filtrationwere filtered
5. 5
   Waschenwashed with n-hexane
6. 6
   workup.STIRRINGstirred for 3 hours
7. 7
   ExtraktionThe organic layer was extracted
8. 8
   Sonstigeseparated
9. 9
   Waschenwashed with water
10. 10
    Trocknendried over MgSO4
11. 11
    Einengenconcentrated

Vorschrift

To a solution of 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitril (2Z compound, 217 mg, 1 mmol) in n-hexane (4 ml) was added a 1 M solution of diisobutylaluminium hydride in toluene (2 ml) with stirring under argon atmosphere at -70° C. After two-hour-stirring at the same temperature, water (0.8 ml) was added to the mixture followed by removal of the cooling bath and vigorous stirring. The resultant while precipitates were filtered and washed with n-hexane. The filtrate was combined with a 10% aqueous solution of oxalic acid and stirred for 3 hours. The organic layer was extracted and separated, washed with water, dried over MgSO4, and concentrated. The above manipulation was conducted under argon atmosphere. The resultant residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=50:1) to obtain the aimed 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienal (198 mg, 90%).

Quelle