تفاعل #5759

معادلة التفاعل

geranial

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

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

المردود 90.0%

المذيبات

n-hexane ethyl acetate

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGwith continuous stirring at the same temperature
2. 2
   درجة الحرارةthe reaction mixture was warmed up to room temperature
3. 3
   استخلاصthe organic layer was extracted
4. 4
   استخلاصThe organic extract
5. 5
   غسيلwas washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزThe filtrate was concentrated
9. 9
   أخرىto give a residue, which

الإجراء التجريبي

To a solution of 2-(diethylphosphono)isovaleronitrile (6.54 g, 30 mmol) in toluene (55 ml) was added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (56 ml) with stirring on a cooling bath at -70° C. After 30 minutes, geranial (3.80 g, 25 mmol) was added thereto with continuous stirring at the same temperature, and then the reaction mixture was warmed up to room temperature. After addition of water to the mixture, the organic layer was extracted. The organic extract was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over MgSO4, and filtered. The filtrate was concentrated to give a residue, which was then subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to give 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile (4.87 g, 90%, 2Z:2E=22.4:1).

المصدر