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2nd September 2013 @ 09:00

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*Reaction file type CDX 

The following is the general method (Method C) for lithiation of ethyl vinyl ether and subsequent alkylation with an alkyl iodide or aldehyde, according to the procedure of Baldwin et al.26

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 1-iodo-4-pentene  (392 mg, 2 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 (224 mg, 80%).

*Yield (%) 80 
*Type of Yield Isolated Product Yield 

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

Further information Compound 315: 2-Ethoxy-1,5-heptadiene

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 317
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