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2nd September 2013 @ 08:24

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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 2-(5-hexenyl)-4,5-dihydrofuran (152 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. Column chromatography of the crude material (SiO2, 10% ether in petrol – 30% ether in petrol) yielded (309) and (310) in 25% and 13% yields respectively. 

*Yield (%) 25 & 13
*Type of Yield Reaction Yield 
Reference(s)

E. Montaudon, R. Lalande, Bull. Soc. Chim. Fr. 1974, 2635.

DavidOwenThesis2000pp45,105,106.pdf
309&310LABBOOK.JPG
 
Further information Compound 309: 2-(1-(E)-Hexenyl)tetrahydrofuran

Compound 310: 3-(2-(E)-Methylcyclohexyliden)-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
DavidOwenThesis2000pp45,105,106.pdf
309&310LABBOOK.JPG
ReactionScheme.gif
ReactionScheme.cdx