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22nd August 2013 @ 10:10

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Reaction information

*#Reaction file  
CSRxnsScheme_108a.cdx
*Reaction file type CDX
*Procedure n-BuLi (0.04 mL of a 2.5 M solution in hexanes, 0.10 mmol) was added dropwise to Cp2ZrCl2 (15.1 mg, 0.05 mmol) in dry THF (2.0 mL) at −78 °C.  The reaction mixture was stirred at −78 °C for 30 mins. Trimethyl(4-(3-pentylidene-2-styrylcyclopentyl)but-1-ynyl)silane (18.8 mg, 0.05 mmol) in dry THF (1.0 mL) was added dropwise at −78 °C.  The reaction mixture was stirred at −78 °C for 20 mins followed by stirring at room temperature for 2 h.  MeOH (5.0 mL) and sat. aq. NaHCO3 solution (5.0 mL) were added and the reaction mixture stirred at room temperature for 16 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 an orange oil (51.6 mg). Purification by column chromatography (SiO2, hexane) and HPLC (hexane) gave the title compound as a colourless oil (11.9 mg, 65%).
*Yield (%)  65
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp71.pdf
AH Thesis_2011_pp168-175.pdf
Further information  Compound 108a: Ethyl(3,5-dimethoxyphenyl)acetate

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp71.pdf
CSRxnsScheme_108a.cdx
AH Thesis_2011_pp168-175.pdf