반응 #5759

반응 방정식

geranial

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

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

수율 90.0%

용매

n-hexane ethyl acetate

toluene

toluene

반응 조건

후처리

1. 1
   workup.STIRRINGwith continuous stirring at the same temperature
2. 2
   온도the reaction mixture was warmed up to room temperature
3. 3
   추출the organic layer was extracted
4. 4
   추출The organic extract
5. 5
   세척was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   농축The filtrate was concentrated
9. 9
   기타to give a residue, which

실험 절차

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).

출처