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20th August 2013 @ 13:39

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Reaction information

*#Reaction file
*Reaction file type CDX
*Procedure  n-BuLi (0.80 mL of a 2.5 M solution in hexanes, 2.0 mmol) was added dropwise to a solution of Cp2ZrCl2 (293 mg, 1.0 mmol) in dry THF (5.0 mL) at −78 °C.  A solution of ynamide (374 mg, 1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C.  The reaction mixture was warmed to room temperature and stirred for 2 h.  The reaction mixture was cooled to 0 °C and iodine (508 mg, 2.0 mmol) and CuCl (99.0 mg, 1.0 mmol) added.  The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into sat. aq. ammonium chloride solution (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with sat. aq. Na2S2O3 solution (100 mL), and sat. aq. NaHCO3 solution (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a brown oil (670 mg). Purification by column chromatography (SiO2, hexane/Et2O 4:1) gave the title compound as an orange oil (416 mg, 66%).
*Yield (%) 66%
*Type of Yield Isolated product yield
AH Thesis_2011_pp176-223.pdf
AH Thesis_2011_pp98.pdf
Further information  Compound 127j: (2E,3Z)-2,3-Bis(1-iodopentylidene)-1-tosylpiperidine

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Overall reaction? True 
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Attached Files
AH Thesis_2011_pp98.pdf
AH Thesis_2011_pp176-223.pdf