반응 #50709

반응 방정식

lithium diisopropylamide

2,6-dicyanotoluene

tetramethyl ethylenediamine

8-phenyloctyl iodide

→

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

용매

tetrahydrofuran

tetrahydrofuran

Water

반응 조건

후처리

1. 1
   온도to warm to 0° C. over one hour
2. 2
   추출extracted with diethyl ether (50 ml)
3. 3
   세척The extracts were washed with 2M hydrochloric acid
4. 4
   기타dried
5. 5
   여과filtered
6. 6
   기타evaporated to a brown oil (2.67 g)
7. 7
   기타Purified by chromatography on flash silica eluting with dichloromethane

실험 절차

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.

출처