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2nd September 2013 @ 09:49

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Reaction information

*#Reaction file
*Reaction file type CDX 

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 using 3-phenyl-4-pentenal (800 mg, 5 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 was purified by Kugelrohr distillation (130 °C, 0.8 mbar) to provide a clear, colourless oil (838 mg, 72%). The product was a 1:1 mixture of diastereomers. 

*Yield (%) 72
*Type of Yield Reaction Yield 

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

K. Omura, D. Swern, Tetrahedron 1978, 34, 1651.

S. L. Huang, K. Omura, D. Swern, Synthesis 1978, 297.

Further information Compound 323: 2-Ethoxy-3-hydroxy-5-phenyl-1,6-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 Reaction 322 
For step in multistep reaction - link to following reaction step N/A
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