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30th August 2013 @ 13:08

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Reaction information

*#Reaction file  
Scheme_387.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 20 minutes.  N-Allyl-N-benzyl-N-(4-octynyl)amine (376, 257 mg, 1.0 mmol) dissolved in THF (2.0 mL) was added dropwise warmed to room temperature, then stirred for 7 hrs before quenching with a saturated solution of NaHCO3 (8.0 mL) and methanol (5.0 mL).  The product was then extracted with 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 pale, oil (143 mg, 0.56 mmol, 56 %).

*Yield (%)  56
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp135.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_387.cdx
DM Thesis_2000_pp135.pdf
DM Thesis_2000_pp51-59.pdf