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29th August 2013 @ 15:22

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Reaction information

*#Reaction file  
Scheme_356.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of 1-benzyl-4,5-di[(E)ethylidene]azepane (347, 0.100 g, 0.41 mmol) in diethyl ether (1.0 mL), under argon, N-phenylmaleimide (0.87 g, 0.50 mmol) was added, and the reaction refluxed for 12 hrs.  The reaction was quenched with methanol (5 mL) and a saturated solution of NaHCO3 (30.0 mL).  The product was extracted into diethyl ether (3 x 50 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.  Radial chromatography (SiO2, 0-100 % Et2O:petroleum followed by 2:1 ethyl acetate:diethyl ether including 5 % Et3N) afforded the title compound as a pale yellow oil (135 mg, 0.3 mmol, 55 %). 

*Yield (%)  55
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp121.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_356.cdx
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp121.pdf