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30th August 2013 @ 13:22

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Reaction information

*#Reaction file  
Scheme_398.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 dropwse and stirred for 20 minutes.  N-Benzyl-N-(4-octynyl)-N-(3-phenyl-2-propynyl)amine (395, 329 mg, 1.0 mmol) in THF (3.0 mL) was added dropwise and the solution warmed to room temperature, strirred for 3 hours.  CuCl (198 mg, 2.0 mmol), sonicated previously and dried under vacuum (0.1 mm Hg), and DMAD (284 mg, 2 mmol) were added to the solution at 0 °C.  The resulting solution was stirred vigorously for 12 hours, HCl (6M, 6 mL) was added and stirred for 2 hours.  The product extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (4 x 50 mL) and brine (50.0 mL) and dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % diethyl ether:petroleum) yielded the title compound as a viscous oil (273 mg, 0.58 mmol, 58 %).

*Yield (%)  58
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp145.pdf
Further information  

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Overall reaction? True
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Attached Files
Scheme_398.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp145.pdf