تفاعل #5762

معادلة التفاعل

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

المردود 84.0%

المذيبات

n-hexane

n-hexane

n-hexane

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىthe cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred well
3. 3
   أخرىResultant white precipitates
4. 4
   ترشيحwere filtered
5. 5
   غسيلwashed
6. 6
   تركيزThe filtrate was concentrated
7. 7
   أخرىto give a residue, which
8. 8
   workup.STIRRINGstirred for 3 hours
9. 9
   استخلاصThe organic layer was extracted
10. 10
    أخرىseparated
11. 11
    غسيلwashed with water
12. 12
    تجفيفdried over MgSO4
13. 13
    تركيزconcentrated

الإجراء التجريبي

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%).

المصدر