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30th August 2013 @ 15:44

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Reaction information

*#Reaction file

*Reaction file type CDX

To a solution of 3,4-dihydro-2H-pyran (631 mg, 7.5 mmol) in THF (8 mL) at –40 °C under Ar, is added dropwise tert-butyllithium (6.1 mL of a 1.3 M solution in pentanes, 8 mmol). The solution is allowed to warm to 0 °C and stirred for 30 minutes before cooling to –20 °C and treatment with a solution of the 1-iodo-5-hexene (1.05 g, 5 mmol) in THF (2 mL). The yellow reaction mixture is allowed to warm to RT and heated at reflux for 1 h. The solution is allowed to cool and poured into saturated NaHCO3 solution (10 mL) and pentane (20 mL). The aqueous layer is separated and extracted with pentane (3 x 50 mL), and the combined organic phases dried over Na2SO4, filtered and concentrated. The crude product was purified by Kugelrohr distillation (100 °C, 0.8 mbar) to give the desired product as a clear, colourless oil (692 mg, 4.17 mmol, 83%). 

*Yield (%) 83
*Type of Yield Isolated Product Yield 

P. J. Kocienski, M. Pritchard, S. N. Wadman, R. J. Whitby, C. L. Yeates, J. Chem. Soc. Perkin Trans. 1 1992, 24, 3419.

Further information Compound 306: 2-(5-Hexenyl)-5,6-dihydro-4H-pyran

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 
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