Réaction #5762

Équation de réaction

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

Rendement 84.0%

Solvants

n-hexane

n-hexane

n-hexane

toluene

Conditions de réaction

Traitement

1. 1
   Autrethe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   AutreResultant white precipitates
4. 4
   Filtrationwere filtered
5. 5
   Lavagewashed
6. 6
   ConcentrationThe filtrate was concentrated
7. 7
   Autreto give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   ExtractionThe organic layer was extracted
10. 10
    Autreseparated
11. 11
    Lavagewashed with water
12. 12
    Séchagedried over MgSO4
13. 13
    Concentrationconcentrated

Mode opératoire

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%).

Source