反応 #5759

反応方程式

geranial

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

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

収率 90.0%

溶媒

n-hexane ethyl acetate

toluene

toluene

反応条件

後処理

1. 1
   workup.STIRRINGwith continuous stirring at the same temperature
2. 2
   温度the reaction mixture was warmed up to room temperature
3. 3
   抽出the organic layer was extracted
4. 4
   抽出The organic extract
5. 5
   洗浄was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮The filtrate was concentrated
9. 9
   その他to give a residue, which

実験手順

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).

出典