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29th August 2013 @ 15:17

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Reaction information

*#Reaction file  
Scheme_349.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of ZrCp2Cl2 (321 mg, 1.1 mmmol) 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. N-Benzyl-N,N-di(3-heptynyl)amine (312, 222 mg, 1.0 mmol) dissolved in THF (3.0 mL) was added and the solution allowed to warm to room temperature.  After 4 hours, at 0 °C, the resulting solution was added to CuCl (198 mg, 2.0 mmol), sonicated previously and dried under vacuum (0.1 mm Hg), and DMAD (284 mg, 2.0 mmol).  The resulting solution was stirred vigorously for 3 hours, then quenched with methanol (5 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) afforded the title compound as a viscous oil (244 mg,  0.56 mmol,  56  %).

*Yield (%)  56
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp117.pdf
Further information  

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Attached Files
Scheme_349.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp117.pdf