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2nd September 2013 @ 13:38

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Reaction information

*#Reaction file  
Scheme_587.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) 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 and stirred for 10 minutes.  N-Methyl-N-[(E)-3-phenyl-2-propenyl]-N-[3-(1,1,1-trimethylsilyl)-2-propynyl]amine (563, 258 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise, the mixture warmed to room temperature, stirred for 5 hrs, before quenching with methanol (5.0 mL) and a saturated solution of NaHCO3 (8.0 mL).  The product extracted into diethyl ether (3 x 100 mL), the combined organic extracts 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 colourless oil (161 mg, 0.61 mmol, 61 %).

*Yield (%)  61
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp184.pdf
Further information  

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Attached Files
Scheme_587.cdx
DM Thesis_2000_pp184.pdf