Reacción #5760

Ecuación de reacción

water

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

diisobutylaluminium hydride

→

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

Rendimiento 90.0%

Disolventes

n-hexane

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   Otrofollowed by removal of the cooling bath and vigorous stirring
3. 3
   OtroThe resultant while precipitates
4. 4
   Filtraciónwere filtered
5. 5
   Lavadowashed with n-hexane
6. 6
   workup.STIRRINGstirred for 3 hours
7. 7
   ExtracciónThe organic layer was extracted
8. 8
   Otroseparated
9. 9
   Lavadowashed with water
10. 10
    Secadodried over MgSO4
11. 11
    Concentraciónconcentrated

Procedimiento

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%).

Fuente