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2nd September 2013 @ 10:29

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Reaction information

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

To a solution of diisopropylamine (13.1 g, 80 mmol) in THF (120 mL), nBuLi (36 mL, 90 mmol) was added dropwise at -80 oC under Ar. The solution was allowed to warm to 0 oC and stirred for an hour. The solution was recooled to -80 oC and ethylphenylacetate (13.1 g, 80 mmol) in THF (20 mL) was added. The solution was allowed to warm to 0 oC and stirred for 1.5 hours. After recooling to -80 oC, allyliodide (13.4 g, 80 mmol) in THF (10 mL) was added. The solition was allowed to warm to room temperature.

H2O (60 mL) was added and stirred for an hour. Then extraction into ether and washed with Na2S2O3, brine, dried over MgSO4, and then concentrated. 
The crude product was purified by Kugelrohr distillation (120 °C, 1 mbar) to provide the desired product (87%).  

*Yield (%) 87
*Type of Yield Isolated Product Yield
Reference(s) A. Padwa, D. J. Austin, A. T. Price, M. A. Semones, M. P. Doyle, M. N. Protopopova, W. R. Winchester, A. Tron, J. Am. Chem. Soc. 1993, 115, 8669. 
Further information Compound 324: Ethyl-(2-phenyl-pent-4-enoate)

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 325
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp48,49,116.pdf