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30th August 2013 @ 13:19

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Reaction information

*#Reaction file  
Scheme_396.cdx
*Reaction file type CDX
*Procedure  

A solution of nBuLi (0.80 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise to a stirred solution of zirconocene dichloride (0.295 g, 1.0 mmol) in THF (2.0 mL) at –78 °C.  N-Benzyl-N-(3-methylthio-(2-propynyl)-N-(4-octynyl)amine (379, 0.300 g, 1.0 mmol) was added to the solution.  The solution was warmed to room temperature and stirred for 7 hours.  The resulting black solution was quenched with methanol (5.0 mL) and a saturated solution of NaHCO3 (5.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), and the combined organic layer washed with water (3 x 50 ml), brine (50.0 mL) dried over MgSO4, filtered and solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title product as a viscous pale yellow oil (0.287 g, 0.9 mmol, 90 %).

*Yield (%)  90
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp142.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
Scheme_396.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp142.pdf