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30th August 2013 @ 13:37

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Reaction information

*#Reaction file
*Reaction file type CDX

To a solution of Cp2ZrCl2 (867 mg, 2.97 mmol) in THF (10 mL) under Ar at –80 °C was added dropwise n-butyllithium (2.4 mL of a 2.5 M solution in hexanes, 5.94 mmol). After 15 minutes a solution of 1-(4-pentenyloxy)-1-heptyne (510 mg, 2.83 mmol) in THF (3 mL) was added. The pale yellow solution was allowed to warm to room temperature and stirred for 4 h. MeOH (2 mL) and saturated NaHCO3 solution (2 mL) were added to the dark red reaction mixture, providing a pale yellow suspension. After 4 h, the mixture was poured into saturated NaHCO3 solution (10 mL) and pentane (20 mL). The layers were separated, and the aqueous extracted with pentane. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (neutral alumina, petrol) to provide the desired product as a pale yellow oil (287 mg, 55%).

*Yield (%) 55
*Type of Yield Isolated Product Yield
Further information Compound 203: 2-[(Z)-Hexylidene]-3-methyltetrahydro-2H-pyran

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 202 
For step in multistep reaction - link to following reaction step N/A
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