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29th August 2013 @ 15:21

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Reaction information

*#Reaction file  
Scheme_355.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) in benzene (1.0 mL), under argon, N-phenylmaleimide (0.087 g, 0.50 mmol) was added.  The reaction refluxed for 16 hrs and then quenched with methanol (5 mL) and a saturated solution of NaHCO3 (30.0 mL). The product was extracted into diethyl ether (3 x 30 mL), the combined organic layer washed with water (3 x 40 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Radial chromatography (SiO2, 0-100 % Et2O:petroleum followed by 9:1 ethyl acetate:diethyl ether) afforded the title compound as a viscous yellow oil (256 mg,   0.65 mmol,  65  %).

*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp120.pdf
DM Thesis_2000_pp40-49.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_355.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp120.pdf