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22nd August 2013 @ 09:17

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Reaction information

*#Reaction file  
CSRxnsScheme_89.cdx
*Reaction file type CDX
*Procedure  n-BuLi (0.60 mL of a 2.5 M solution in hexanes, 1.5 mmol) was added dropwise to a solution of Cp2ZrCl2 (219 mg, 0.80 mmol) in dry THF (5.0 mL) at −78 °C. Enediyne 78 (194 mg, 0.80 mmol) in dry THF (3.0 mL) was added dropwise to the reaction mixture at −78 °C.  The reaction mixture was warmed to room temperature over 1 h and left stirring at room temperature for 4 h.  HCl (2.0 mL of a 2 M solution in Et2O) was added dropwise to the reaction mixture and left stirring overnight.  The reaction mixture was poured into water (100 mL) and extracted with ether (2 × 75 mL).  The organic extracts were combined, washed sequentially with water (75 mL) and sat. aq. NaHCO3 solution (75 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (199 mg). Purification by column chromatography (SiO2, hexane) gave the title compound as an orange oil (39.0 mg, 20%).
*Yield (%)  20
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp61.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 89: 2-Methyl-1-(oct-3-ynyl)-3-pentylidenecyclopentane

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp61.pdf
CSRxnsScheme_89.cdx
AH Thesis_2011_pp145-167.pdf