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30th August 2013 @ 13:13

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Reaction information

*#Reaction file  
Scheme_391.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 was added dropwise, nBuLi (0.8 mL of 2.5 M solution in hexanes, 2.0 mmol) and left for 10 minutes.  Allyl-benzyl-(2-pent-1-ynyl-benzyl)-amine (382, 304 mg, 1.0 mmol) in THF (2.0 mL) was added dropwise and the mixture warmed to room temperature before stirring for 7 hrs.  The reaction was quenched with methanol (5 mL) and a saturated solution of NaHCO3 (8.0 mL).  The product was extracted into diethyl ether (3 x 100 mL), the 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 compound as a viscous oil (185 g, 0.61 mmol, 61 %).

*Yield (%)  61
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp138.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_391.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp138.pdf