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30th August 2013 @ 13:20

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in dry THF (5 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-Benzyl-N-(3-methylthio-(2-propynyl)-N-(4-octynyl)amine (378, 299 mg, 1.0 mmol) as a solution in THF (3 mL) was added dropwise and the solution was allowed to warm to room temperature.  After stirring for 4 hours CuCl (198 mg, 2.0 mmol), sonicated previously and dried under vacuum (0.1 mm Hg), and DMAD (284 mg, 2.0 mmol) were added.  The resulting solution was stirred for 12 hours, HCl (6M, 6 mL) was added to the resulting black solution.  The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (4 x 50 mL) and brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Purification by column chromatography (SiO2, 0-100 % Et2O:petroleum) afforded the title compound as a viscous oil (269 mg, 0.56 mmol,  61 %).  

*Yield (%)  61
*Type of Yield Isolated product yield
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp143.pdf
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Attached Files
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp143.pdf