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29th August 2013 @ 15:19

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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 of 2.5 M solution in hexanes, 2.0 mmol) was added dropwise. Benzyl-hept-3-ynyl-(4-methylsulfanyl-but-3-ynyl)-amine (314, 299 mg, 1.0 mmol) in THF (3.0 mL) was added, warmed to room temperature, and stirred for 3 hours.  After this, 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 to the solution.  The reaction was stirred vigorously for 3 hours, then quenched with methanol and a saturated solution of NaHCO3 (10.0 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 (202 mg,  0.56 mmol,  56 %).

*Yield (%)  56
*Type of Yield Isolated product yield
DM Thesis_2000_pp118.pdf
DM Thesis_2000_pp40-49.pdf
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Attached Files
DM Thesis_2000_pp118.pdf
DM Thesis_2000_pp40-49.pdf