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30th August 2013 @ 13:12

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Reaction information

*#Reaction file  
Scheme_390.cdx
*Reaction file type CDX
*Procedure  To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in dry THF (5 mL) under argon at 80 °C, nBuLi (0.8 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise and left for 10 minutes. Benzyl-but-2-ynyl-pent-4-enyl-amine (289, 213 mg, 1.0 mmol) dissolved in THF (2.0 mL) was added dropwise.  The solution was warmed to room temperature, stirred for 7 hrs before quenching with a saturated solution of NaHCO3 (8.0 mL) and methanol (5.0 mL).  The product was 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 compound as a pale oil (168 mg, 0.78 mmol, 78 %).
*Yield (%)  78
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp137.pdf
Further information  

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Overall reaction? True
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Attached Files
Scheme_390.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp137.pdf