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2nd September 2013 @ 13:16

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Reaction information

*#Reaction file  
Scheme_552.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, nBuLi (0.8 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise and stirred for 10 minutes.  N-(2-Butynyl)-N-methyl-N-(2-phenylallyl)amine (536, 200 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise and the solution allowed to warm to room temperature, then left to stir for 5 hrs before quenching with methanol (5.0 mL) and a saturated solution of NaHCO3 (8.0. 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 pale, viscous oil (103 mg, 0.51 mmol, 51 %).

*Yield (%)  51
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp81-89.pdf
DM Thesis_2000_pp168.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  
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Attached Files
DM Thesis_2000_pp81-89.pdf
Scheme_552.cdx
DM Thesis_2000_pp168.pdf