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30th August 2013 @ 13:54

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Reaction information

*#Reaction file  
Scheme_411.cdx
*Reaction file type CDX
*Procedure  

To a stirring solution of titanium isopropoxide (2.5 mmol, 0.74 mL), Et2O (10.0 mL), and iPrMgCl (2.75 mL, 5.5 mmol) at – 78 °C, N-allyl-N-methyl-N-(3-phenyl-3-butenyl)amine (412, 201.0 mg, 1.0 mmol) was added dropwise.  The mixture was stirred at –50 °C for 1 hour, then warmed to between –40 °C and –30 °C for 5 hours.  When no starting material remained (GC analysis) the reaction was quenched by the addition of methanol (6.0 mL) and a saturated solution of NaHCO3 (8.0 mL).  The product was extracted into diethyl ether (3 x 100 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.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound (12 mg, 0.12 mmol, 12 %). 

*Yield (%)  12
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp149.pdf
DM Thesis_2000_pp64.pdf
Further information  

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Overall reaction? True
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For step in multistep reaction - link to previous reaction step  
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Attached Files
DM Thesis_2000_pp64.pdf
Scheme_411.cdx
DM Thesis_2000_pp149.pdf