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30th August 2013 @ 15:55

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Reaction information

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

To a solution of ZrCp2Cl2 (321 mg, 1.1 mmol) in THF (5 mL) at –80 °C under Ar is added dropwise n-butyllithium (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol). In the case of substrates containing a free hydroxyl group, 2.2 equivalents of ZrCp2Cl2 (642 mg) and 4.4 equivalents of n-butyllithium (1.76 mL) are used. After the addition of butyllithium, a solution of the 5-(3-phenyl-4-pentenyl)-2,3-dihydrofuran (214 mg, 1 mmol) in THF (2 mL) is added dropwise and the solution allowed to warm to RT. After between 3 h and 16 h at RT, MeOH (3 mL) and saturated NaHCO3 solution (7 mL) are added and the cloudy white or pale yellow reaction mixture stirred for between 2 h and 16 h. After dilution of the reaction mixture with ether (20 mL) and water (20 mL), the aqueous phase is separated and extracted with ether (3 x 50 mL). The combined organic phases are combined and washed with brine, dried over MgSO­4, filtered and concentrated. The crude product was purified by column chromatography (SiO2, 20% ether in hexane) to provide the desired product as a viscous, clear colourless oil (150 mg, 69% yield). This product was obtained as a single diastereomer. 

*Yield (%) 69 
*Type of Yield Isolated Product Reaction 
Reference(s)

E. Negishi, F. E. Cederbaum, T. Takahashi, Tetrahedron Lett. 1986, 27, 2829.

DavidOwenThesis2000pp43,44,105.pdf
308LABBOOK.JPG
Further information Compound 308: (2S*,3R*)-3-(2-Methyl-3-phenylcyclopentyliden)-1-propanol

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 
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp43,44,105.pdf
308LABBOOK.JPG