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30th August 2013 @ 13:22

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Reaction information

*#Reaction file  
Scheme_400.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of methyl vinyl ketone (77.0 mg, 1.1 mmol), dissolved in benzene (1 mL), 4-[(E)Butylidene]-3-[(Z)-1-(methylthio)methylidene]-1-(phenylmethyl)perhydroazepine (396), 304 mg, 1.0 mmol) was added dropwise.  The solution was refluxed for 12 hours, quenched with methanol (5 mL) and a saturated solution of NaHCO3 (40.0 mL).  The product was extracted into diethyl ether (3 x 30 mL), the combined organic layer washed with water (3 x 30 ml), brine (30.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Radial chromatography (SiO2, 5% Et2O:petroleum including 5 % Et3N) afforded the title compound as a pale oil (0.156 g, 0.42 mmol, 56 %).

*Yield (%)  56
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp146.pdf
DM Thesis_2000_pp51-59.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_400.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp146.pdf