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2nd September 2013 @ 13:09

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Reaction information

*#Reaction file  
Scheme_456.cdx
*Reaction file type CDX
*Procedure  

To a solution of zirconocene dichloride (0.321 g, 1.0 mmol) in THF (2.0 mL) at –78 °C nBuLi (0.80 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise over 5 minutes.  After stirring for 5 minutes, methyl-pent-3-ynyl-(3-phenyl-prop-2-ynyl)-amine (452, 211 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise to the yellow solution, warmed to room temperature, and stirred for 7 hours.  The resulting black solution quenched with methanol (5.0 mL) and NaHCO3 (5.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), 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 (165 mg, 0.78 mmol, 78 %).

*Yield (%)  78
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp70-75.pdf
DM Thesis_2000_pp161.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_456.cdx
DM Thesis_2000_pp70-75.pdf
DM Thesis_2000_pp161.pdf