反应 #5761

反应方程式

farnesol

2-(diethylphosphono)isovaleronitrile

potassium bis(trimethylsilyl)amide

water

→

2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

收率 96.0%

溶剂

toluene

toluene

反应条件

后处理

1. 1
   其他The cooling bath was removed
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 30 minutes
3. 3
   温度The reaction mixture was cooled to -70° C. again
4. 4
   workup.STIRRINGwith stirring
5. 5
   温度to warm to room temperature
6. 6
   其他the organic layer was separated
7. 7
   洗涤washed with saturated aqueous sodium bicarbonate
8. 8
   干燥saturated aqueous sodium chloride, and dried over MgSO4
9. 9
   其他The organic layer was separated from MgSO4 by filtration
10. 10
    浓缩concentrated
11. 11
    其他to give a residue, which
12. 12
    其他was purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1)

实验过程

To a solution of 2-(diethylphosphono)isovaleronitrile (8.72 g, 40 mmol) in toluene (75 ml) was gradually added a 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (75 ml) with stirring at -70° C. under argon atmosphere. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to -70° C. again, and farnesol (5.88 g, 26.7 mmol) was added thereto with stirring, and the mixture was allowed to warm to room temperature. After addition of water, the organic layer was separated, washed with saturated aqueous sodium bicarbonate and then saturated aqueous sodium chloride, and dried over MgSO4. The organic layer was separated from MgSO4 by filtration and concentrated to give a residue, which was purified with silica gel column chromatography (solvent: n-hexane/ethyl acetate=100:1) to obtain the aimed 2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (7.23 g, 96%; 2Z:2E=25.6:1).

来源