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Reaction 99: Zirconocene mediated tandem tricyclisations
22nd August 2013 @ 10:05

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Reaction information

*#Reaction file
CSRxnsScheme_99.cdx
*Reaction file type CDX
*Procedure n-BuLi (0.25 mL of a 2.5 M solution in hexanes, 0.62 mmol) was added dropwise to Cp2ZrCl2 (91 mg, 0.31 mmol) in dry THF (2.0 mL) at −78 °C.  The reaction mixture was stirred at −78 °C for 30 mins. Trimethyl(5-vinyltrideca-1,8-diynyl)silane (85 mg, 0.31 mmol) in dry THF (1.0 mL) was added dropwise at −78 °C.  The reaction mixture was stirred at −78 °C for 30 mins followed by stirring at room temperature for 2 h. Benzyl chloride (0.04 mL, 0.33 mmol) and LiTMP [prepared by dropwise addition of n-BuLi (0.12 mL of a 2.5 M solution in hexanes, 0.31 mmol) to TMP (0.06 mL, 0.33 mmol) in dry THF (1.00 mL) at 0 °C and stirring at 0 °C for 30 mins] were added dropwise sequentially at −78­ °C.  After stirring at −78 °C for 30 mins the reaction mixture was stirred at room temperature for 18 h.  MeOH (5.0 mL) and sat. aq. NaHCO3 solution (5.0 mL) were added and the reaction mixture stirred at room temperature for 8 h.  The reaction mixture was poured into water (50 mL) and extracted with ether (3 × 25 mL).  The organic extracts were combined, washed sequentially with water (3 × 50 mL) and brine (50 mL) dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a yellow oil (213 mg). Purification by column chromatography (SiO2, hexane) and HPLC (hexane) gave the title compound as a colourless oil (29.3 mg, 26%).
*Yield (%)  26
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp65.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 99: Trimethyl(4-(3-pentylidene-2-styrylcyclopentyl)but-1-ynyl)silane

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Overall reaction? True
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Attached Files
CSRxnsScheme_99.cdx
AH Thesis_2011_pp65.pdf
AH Thesis_2011_pp145-167.pdf
Hartke A. (ah31g11) | View Source | A.Henderson | Comments (0)
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