All Notebooks | Help | Support | About
29th August 2013 @ 15:10

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file  
Scheme_343.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in dry THF (5.0 mL) under argon at 80 °C, nBuLi (0.8 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise and then stirred for 20 minutes. N-Benzyl-N-(3-butenyl)-N-(3-heptynyl)amine (310, 0.221 g, 1 mmol) in THF (2.0 mL) was added dropwise to the solution warmed to room temperature, and stirred for 7 hrs.  The reaction was quenched with methanol (5.0 mL) and a saturated solution of NaHCO3 (8.0 mL).  The product extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (4 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title product as a pale viscous oil (138 mg, 0.54 mmol, 54 %).

*Yield (%)  54
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp111.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
DM Thesis_2000_pp40-49.pdf
Scheme_343.cdx
DM Thesis_2000_pp111.pdf