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2nd September 2013 @ 13:36

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Reaction information

*#Reaction file  
Scheme_578.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-Allyl-N-methyl-N-[(Z)-3-phenyl-2-propenyl]amine (558, 188 mg, 1.0 mmol) as a solution in THF (2.0 mL) was added dropwise, warmed to room temperature stirred for 5 hrs.  After cooling to –78 °C the solution was added to a stirring solution of CuI (2.0 mmol, 380.0 mg) and allyl bromide (2.0 mmol, 240 mg).  The resulting mixture was stirred for 12 hours before quenching with methanol (8.0 mL) and a saturated solution of NaHCO3 (8.0 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 colourless oil (213 mg, 0.79 mmol, 79 %).

*Yield (%)  79
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp91-95.pdf
DM Thesis_2000_pp182.pdf
Further information  

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Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
Scheme_578.cdx
DM Thesis_2000_pp91-95.pdf
DM Thesis_2000_pp182.pdf