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2nd September 2013 @ 08:51

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Reaction information

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

To a solution of ethyl vinyl ether (0.95 mL, 721 mg, 10 mmol) in THF (8 mL) at –70 °C under Ar is added dropwise tert-butyllithium (4.7 mL of a 1.7 M solution in pentanes, 8 mmol), resulting in a bright yellow suspension. The reaction is allowed to warm, resulting in dissolution of the yellow precipitate, and disappearance of the yellow colour at around 0 °C. The solution is re-cooled to –70 °C and a solution of the 1-iodo-5-hexene (2.10 g, 10 mmol) in THF (2 mL) is added. After warming to 0 °C and stirring for between 1 h and 5 h, saturated NH4Cl solution (10 mL) is added. After dilution with ether (20 mL), the aqueous phase is separated and extracted with ether (3 x 50 mL), and the combined organic phases washed with brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by Kugelrohr distillation yielding a clear, colourless oil (1.457 g, 95%).

*Yield (%) 95 
*Type of Yield Isolated Product Yield 
Reference(s)

J. E. Baldwin, G. A. Hofle, O. W. Lever, J. Am. Chem. Soc. 1974, 96, 7125.

DavidOwenThesis2000pp47,111.pdf
316LABBOOK.JPG
Further information Compound 316: 2-Ethoxy-1,7-octadiene

For multistep reactions (or their steps):

Overall reaction? True
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 N/A 
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp47,111.pdf
316LABBOOK.JPG