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2nd September 2013 @ 08:47

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Reaction information

*#Reaction file
*Reaction file type CDX 

To a solution of Cp2ZrCl2 (964 mg, 3.3 mmol) in THF (15 mL) at –80 °C under Ar was added dropwise n-butyllithium (2.64 mL of a 2.5 M solution in hexanes, 6.6 mmol). After 10 min 2-(5-hexenyl)-5,6-dihydro-4H-pyran (498 mg, 3 mmol) in THF (3 mL) was added. The solution was allowed to warm to room temperature and stirred for 3 h. 7 mL (one third) of the reaction mixture was removed and added to a stirred mixture of MeOD (1 mL) and D2O (2 mL) and quenched for 1 h. The remainder of the reaction mixture was quenched with MeOH (3 mL) and saturated NaHCO3 solution (6 mL) for 1 h. The products of both quenches were worked up and purified identically: The white suspension was diluted with water and ether, and the aqueous phase separated and extracted with ether. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The crude oils were purified by column chromatography (SiO2, 5% ether in petrol). The protic quenched product (314a) was obtained in 35% yield (116 mg) and the deuterium quenched product (314b) in 30% yield (51 mg). Both were clear, colourless oils. 

*Yield (%)  35 & 30
*Type of Yield Isolated Product Yield 

F. Balzano, C. Malanga, R. Menicagli, Synth. Commun. 1997, 27, 1509.

A. F. Thomas, Total Synthesis of Natural Products, Vol. 2, J. Wiley & Sons, New York 1973, p167.

Further information Compound 314a: 2-[(E)-1-Hexenyl]-tetrahydro-2H-pyran

Compound 314b: 2-[(E)-1-Hexenyl]-2,3-dideutero-tetrahydro-2H-pyran

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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