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30th August 2013 @ 13:29

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Reaction information

*#Reaction file  
Scheme_405.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of methyl propriolate (84.0 mg, 1.0 mmol) and boron trifluoride diethyl ether complex (0.40 mL, 3.0 mmol) dissolved in dichloromethane (1.0 mL) at –78 °C, 4-[(E)Butylidene]-3-[(Z)-1-(methylthio)methylidene]-1-(phenylmethyl)perhydroazepine (396, 0.304 g, 1.0 mmol) was added dropwise, warmed to room temperature and refluxed for 1 hrs.  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 solvent removed under reduced pressure.  The title compound was isolated as a pale oil (162 mg, 0.48 mmol, 48 %).

 

*Yield (%)  48
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp148.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_405.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp148.pdf