반응 #5762

반응 방정식

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

수율 84.0%

용매

n-hexane

n-hexane

n-hexane

toluene

반응 조건

후처리

1. 1
   기타the cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   기타Resultant white precipitates
4. 4
   여과were filtered
5. 5
   세척washed
6. 6
   농축The filtrate was concentrated
7. 7
   기타to give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   추출The organic layer was extracted
10. 10
    기타separated
11. 11
    세척washed with water
12. 12
    건조dried over MgSO4
13. 13
    농축concentrated

실험 절차

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%).

출처