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29th August 2013 @ 15:20

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Reaction information

*#Reaction file  
Scheme_354.cdx
*Reaction file type CDX
*Procedure  

To a stirring solution of 1-benzyl-4,5-di[(E)butylidene]azepane (344, 0.297 g, 1.0 mmol) in benzene (1.0 mL), under argon, N-phenylmaleimide (0.190 g, 1.1 mmol) was added dropwise.  The reaction was refluxed for 15 hrs and then quenched with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted with 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 then 50% ethyl acetate:petroleum including 5 % Et3N) afforded the title compound as a viscous yellow oil (365 mg, 0.77 mmol, 77 %).

*Yield (%)  77
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp119.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_354.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp119.pdf