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30th August 2013 @ 13:16

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Reaction information

*#Reaction file  
Scheme_394.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of ZrCp2Cl2 (321 mg, 1.1 mmol) in dry 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-(3-methylsulfanyl-prop-2-ynyl)-(2-pent-1-ynyl-benzyl)-amine (383, 347 mg, 1.0 mmol) in THF (3.0 mL) was added and the solution was allowed to warm to room temperature.  After 4 hours, at 0 °C, the resulting solution was added by cannula addition to CuCl (198 mg, 2.0 mmol), sonicated previously and dried under vacuum (0.1 mm Hg), and DMAD (284 mg, 2.0 mmol).  The resulting solution was then stirred vigorously for 12 hours, NaHCO3 (6.0 mL, 6M) was added to the resulting dark brown solution.  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 (319 mg,  0.65 mmol,  65 %).

*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp140.pdf
Further information  

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
Scheme_394.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp140.pdf