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30th August 2013 @ 13:02

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Reaction information

*#Reaction file  
Scheme_381.cdx
*Reaction file type CDX
*Procedure  

A solution of propargylbenzylamine (8.7 g, 8.9 mL, 60.0 mmol) in methanol (25.0 mL) was acidified with HCl (6M, 4.0 mL) before adding 2-(1-pentynyl)benzaldehyde (380, 1.96 g, 10.0 mmol).  After 15 minutes, sodium triacetoxyborohydride (6.4 g, 30.0 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 (758 g, 2.5 mmol, 25 %).

*Yield (%)  25
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp131.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
DM Thesis_2000_pp131.pdf
Scheme_381.cdx
DM Thesis_2000_pp51-59.pdf