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29th August 2013 @ 15:25

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Reaction information

*#Reaction file  
Scheme_358.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of 4,5-di[(E)butylidene]-1-methylazepane (346, 0.111 g, 0.50 mmol) and boron trifluoride diethyl etherate complex (0.30 mL, 2.0 mmol)  in dichloromethane (1.0 mL), 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione (100 mg, 0.59 mmol) in THF (3.0 mL) at – 78 °C was added.  The mixture was warmed to room temperature, stirred for 2 hours and quenched with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Radial chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a viscous yellow oil (240 mg,  0.54 mmol, 54 %).

*Yield (%)  54
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp123.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  
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Attached Files
Scheme_358.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp123.pdf