All Notebooks | Help | Support | About
20th August 2013 @ 13:39

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file
CSRxnsScheme_127j.cdx
*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
Reference(s)  
AH Thesis_2011_pp176-223.pdf
AH Thesis_2011_pp98.pdf
Further information  Compound 127j: (2E,3Z)-2,3-Bis(1-iodopentylidene)-1-tosylpiperidine

For multistep reactions (or their steps):

Overall reaction? True 
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp98.pdf
AH Thesis_2011_pp176-223.pdf
CSRxnsScheme_127j.cdx