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20th August 2013 @ 13:43

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Reaction information

*#Reaction file
CSRxnsScheme_128a.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 (360 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 1.5 h.  The reaction mixture was cooled to 0 °C.  CuCl (297 mg, 3.0 mmol) and DMAD (0.25 mL, 2.0 mmol) were added.  The reaction mixture was warmed to room temperature and stirred for 6.5 h.  Water (10.0 mL) was added and the reaction mixture stirred at room temperature for 16 h.  The reaction mixture was poured into water (200 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed with brine (2 × 200 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (602 mg). Purification by column chromatography (SiO2, hexane/Et2O 4:1 ® 1:1) gave the title compound as an orange oil (259 mg, 52%). 
*Yield (%)  52
*Type of Yield Isolated product yield
Reference(s)
AH Thesis_2011_pp98.pdf
AH Thesis_2011_pp176-223.pdf
Further information Compound 128a: Dimethyl-4,7-dibutyl-1-tosylindoline-5,6-dicarboxylate

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_128a.cdx