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29th August 2013 @ 15:08

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Reaction information

*#Reaction file  
Scheme_333.cdx
*Reaction file type CDX
*Procedure  

To a stirred solution of ZrCp2Cl2 (0.292 g, 1.0 mmol) in pre-dried THF (5.0 mL) under argon at –80 °C, nBuLi (0.8 mL, 2.5 M solution in hexanes, 2.0 mmol) was added dropwise and the reaction stirred for 30 minutes.  N,N-Di(3-butenyl)-N-methylamine (305, 0.140, 1.0 mmol) in THF (3.0 mL) was added dropwise and the reaction warmed to room temperature.  The reaction was stirred for 6 hours, before quenching with a saturated solution of methanol (5.0 mL) and NaHCO3 (8.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), and the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure at 0 °C.  Kugelrohr distillation (130 °C and 120 torr) afforded the title compound (107 mg, 0.75 mmol, 75  %).

 

*Yield (%)  75
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp40-49.pdf
DM Thesis_2000_pp109.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
DM Thesis_2000_pp40-49.pdf
Scheme_333.cdx
DM Thesis_2000_pp109.pdf