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29th August 2013 @ 15:15

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Reaction information

*#Reaction file  
Scheme_347.cdx
*Reaction file type CDX
*Procedure  

To a stirring solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in pre-dried 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 stirred at –78 ° C for 10 minutes.  N-Benzyl-N,N-di(3-pentynyl)amine (311, 240 mg, 1.0 mmol) as a solution in THF (3.0 mL) was added, warmed to room temperature and stirred for 5 hours.  The reaction was quenched with methanol (3.0 mL) and a saturated solution of NaHCO3 (6.0 mL).  The product was 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 compound as a viscous yellow oil (0.191 g, 0.79 mmol, 79 %).

*Yield (%)  79
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp115.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  
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Attached Files
DM Thesis_2000_pp40-49.pdf
Scheme_347.cdx
DM Thesis_2000_pp115.pdf