Реакция #5760

Уравнение реакции

water

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

diisobutylaluminium hydride

→

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

Выход 90.0%

Растворители

n-hexane

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   Другоеfollowed by removal of the cooling bath and vigorous stirring
3. 3
   ДругоеThe resultant while precipitates
4. 4
   Фильтрацияwere filtered
5. 5
   Промывкаwashed with n-hexane
6. 6
   workup.STIRRINGstirred for 3 hours
7. 7
   ЭкстракцияThe organic layer was extracted
8. 8
   Другоеseparated
9. 9
   Промывкаwashed with water
10. 10
    Сушкаdried over MgSO4
11. 11
    Концентрированиеconcentrated

Методика

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%).

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