反应 #50709

反应方程式

lithium diisopropylamide

2,6-dicyanotoluene

tetramethyl ethylenediamine

8-phenyloctyl iodide

→

2-(9-phenylnonyl)-1,3-benzenedicarbonitrile

溶剂

tetrahydrofuran

tetrahydrofuran

Water

反应条件

后处理

1. 1
   温度to warm to 0° C. over one hour
2. 2
   萃取extracted with diethyl ether (50 ml)
3. 3
   洗涤The extracts were washed with 2M hydrochloric acid
4. 4
   其他dried
5. 5
   过滤filtered
6. 6
   其他evaporated to a brown oil (2.67 g)
7. 7
   其他Purified by chromatography on flash silica eluting with dichloromethane

实验过程

A solution of lithium diisopropylamide 1.5M in tetrahydrofuran (6 ml, 9 mmol) was added dropwise to a stirred solution of 2,6-dicyanotoluene (0.85 g, 6 mmol) and tetramethyl ethylenediamine (1.04 g, 9 mmol) in dry tetrahydrofuran (50 ml), cooled to -70° C. under nitrogen. After one hour, 8-phenyloctyl iodide (2.15 g, 6.8 mmol) was added dropwise at -70° C. to the intense blue suspension, then allowed to warm to 0° C. over one hour. Water (100 ml) was added (cautiously at first) to the brown mixture and then extracted with diethyl ether (50 ml). The extracts were washed with 2M hydrochloric acid, dried, filtered and evaporated to a brown oil (2.67 g). Purified by chromatography on flash silica eluting with dichloromethane gave 2-(9-phenylnonyl)-1,3-benzenedicarbonitrile as an oil.

来源