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29th August 2013 @ 15:11

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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 stirred for 10 minutes.  N-Benzyl-N,N-di(3-heptynyl)amine (312, 0.295 g, 1.0 mmol) in THF (3.0 mL) was added to the reaction, which was warmed to room temperature, and stirred for 8 hours.  The reaction was quenched with methanol (3.0 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 diene as a viscous oil (0.273 g, 0.92 mmol, 92 %).

*Yield (%)  92
*Type of Yield Isolated product yield
DM Thesis_2000_pp112.pdf
DM Thesis_2000_pp40-49.pdf
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Attached Files
DM Thesis_2000_pp112.pdf
DM Thesis_2000_pp40-49.pdf