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29th August 2013 @ 15:16

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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 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 stirrred for 20 minutes.  N,N-Di(3-heptynyl)-N-methylamine (313, 222 mg, 1.0 mmol) in THF (3.0 mL) was added, warmed to room temperature and the reaction stirred.  After 4 hours, at 0 °C, CuCl (198 mg, 2.0 mmol), pre-sonicated and dried under vacuum (0.1 mm Hg), and DMAD (284 mg, 2.0 mmol) were added.  The resulting solution was stirred vigorously for 4 hours, quenched with methanol (5.0 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 oil (166 mg,  0.46 mmol,  46 %).

*Yield (%)  46
*Type of Yield Isolated product yield
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp116.pdf
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Attached Files
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp116.pdf