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30th August 2013 @ 14:08

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Reaction information

*#Reaction file  
Scheme_418.cdx
*Reaction file type CDX
*Procedure  

To a stirred mixture of 3-butyn-1-ol (26.0 g, 400.0 mmol) and iron powder (0.45 g) was added to hydrobromic acid (48 % in water, 97.0 g, 1.20 mol).  The mixture was stirred at room temperature overnight and then at 70 °C for 3 hours before quenching with a saturated solution of NaHCO3 (40.0 mL).  The product was extracted with Et2O (250.0 mL), the extracts washed with water (3 x 50.0 mL), brine (100.0 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 pale yellow oil (6.02 g, 28.1 mmol, 8 %).

*Yield (%)  8
*Type of Yield Isolated product yield
Reference(s)  
DM Thesis_2000_pp155.pdf
DM Thesis_2000_pp64.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_pp64.pdf
Scheme_418.cdx
DM Thesis_2000_pp155.pdf