反応 #5762

反応方程式

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

収率 84.0%

溶媒

n-hexane

n-hexane

n-hexane

toluene

反応条件

後処理

1. 1
   その他the cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   その他Resultant white precipitates
4. 4
   ろ過were filtered
5. 5
   洗浄washed
6. 6
   濃縮The filtrate was concentrated
7. 7
   その他to give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   抽出The organic layer was extracted
10. 10
    その他separated
11. 11
    洗浄washed with water
12. 12
    乾燥dried over MgSO4
13. 13
    濃縮concentrated

実験手順

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%).

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