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30th August 2013 @ 14:20

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Reaction information

*#Reaction file  
Scheme_422.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, allyl-benzyl-(3-phenyl-but-3-enyl)-amine (421, 277 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise, warmed to room temperature and stirred for 10 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), 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 (106 mg, 0.4 mmol, 38 %).

*Yield (%)  38
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp64.pdf
DM Thesis_2000_pp158.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_pp64.pdf
Scheme_422.cdx
DM Thesis_2000_pp158.pdf