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2nd September 2013 @ 08:32

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Reaction information

*#Reaction file
*Reaction file type CDX 

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 (4-octynyl)-4,5-dihydrofuran (178 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 material was purified by column chromatography (SiO­2, petrol – 20% ether – 40% ether gradient) to give the title compounds. The alcohol (311) was obtained as a clear, colourless oil (73 mg, 41%). The triene (312) was also obtained as a clear, colourless oil (45 mg, 28%), contaminated with a small amount of material derived from a slight impurity in the starting enyne. 

*Yield (%) 41 & 28
*Type of Yield Reaction Yield
Further information Compound 311: 3-{2-[(E)-Butylidene]cyclopentyliden}-1-propanol

Compound 312: 3-{2-[(E)-butyl-idene] cyclopentyliden}-2-propene

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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