Reacción #5762

Ecuación de reacción

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

Rendimiento 84.0%

Disolventes

n-hexane

n-hexane

n-hexane

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   OtroResultant white precipitates
4. 4
   Filtraciónwere filtered
5. 5
   Lavadowashed
6. 6
   ConcentraciónThe filtrate was concentrated
7. 7
   Otroto give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   ExtracciónThe organic layer was extracted
10. 10
    Otroseparated
11. 11
    Lavadowashed with water
12. 12
    Secadodried over MgSO4
13. 13
    Concentraciónconcentrated

Procedimiento

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%).

Fuente