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30th August 2013 @ 13:18

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Reaction information

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

A solution of 4-pentene-1-ol (4.306 g, 50 mmol) in THF (20 mL) was added to a solution of pentane washed sodium hydride (1.92 g, 48 mmol) in THF (35 mL) and the mixture stirred until effervescence ceased (3 h). Trichloroethene (4.13 mL, 6.04 g, 46 mmol) was added and the solution heated to reflux overnight. After cooling, MeOH (10 mL), H2O (25 mL) and Et2O (50 mL) were added. The layers were separated and the aqueous layer extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filteredand concentrated to give an orange oil. The crude product was purified by column chromatography (SiO2, petrol) to give the title compound as a clear, colourless oil (5.614 g, 67%).

*Yield (%) 67
*Type of Yield Isolated Product Yield
Reference(s)
DavidOwenThesis2000pp35,36,90,91.pdf
Further information Compound 201: 5-((1,2-Dichloro-1-ethenyl)oxy)-1-pentene

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A
For step in multistep reaction - link to previous reaction step N/A
For step in multistep reaction - link to following reaction step Reaction 202
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp35,36,90,91.pdf