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2nd September 2013 @ 09:04

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a solution of Cp2ZrCl2 (321 mg, 1.1 mmol) in THF (5 mL) at –80 °C under Ar was added dropwise n-butyllithium (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol), followed by a solution of 2-ethoxy-1,6-heptadiene (140 mg, 1 mmol) in THF (2 mL). The solution was allowed to warm to room temperature and stirred for 3 h. The orange solution was re-cooled to –80 °C and iodine (254 mg, 1 mmol) in THF (2 mL) was added. The solution was allowed to warm to 0 °C and quenched with 2 M HCl (6 mL). The mixture was extracted with pentane and the organic phases washed with saturated Na2S2O3 solution and brine, dried over MgSO4, filtered and concentrated to give a brown oil. Purification by column chromatography (SiO2, pentane) removed much of the coloured and inorganic material, but resulted in some decomposition of the product. The iodide was obtained in 45% yield, and about 80% purity. 

*Yield (%) 45 
*Type of Yield Reaction Yield

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

Further information Compound 317: 2-Methylene-1-(iodomethyl)cyclopentane

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 315 
For step in multistep reaction - link to following reaction step N/A
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