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30th August 2013 @ 13:03

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Reaction information

*#Reaction file  
Scheme_382.cdx
*Reaction file type CDX
*Procedure  

A solution of N-allylbenzylamine (4.42 g, 4.5 mL, 30.0 mmol) in methanol (25.0 mL) was acidified with HCl (6.0 M, 4.0 mL) before adding 2-(1-pentynyl)benzaldehyde (380, 1.05 g, 5 mmol).  After 15 minutes, sodium triacetoxyborohydride (6.30 g, 30 mmol) was added and stirred for 72 hours before quenching with a saturated solution of NaHCO3 (100.0 mL). The product was extracted into diethyl ether (3 x 50 mL), 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.  Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a yellow oil (456 g, 1.5 mmol, 35 %).

*Yield (%)  35
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp132.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_382.cdx
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp132.pdf