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2nd September 2013 @ 11:06

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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 2-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 (100 °C, 1 mbar) to provide pure material as a clear colourless oil (808 mg, 70%). The product was a single diastereomer.

*Yield (%) 70 
*Type of Yield Isolated Product Yield
Further information Compound 327: (3R*,4S*)-2-Ethoxy-3-hydroxy-4-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 326 
For step in multistep reaction - link to following reaction step N/A
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