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22nd August 2013 @ 13:41

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Reaction information

*#Reaction file  
CSRxnsScheme_117i.cdx
*Reaction file type CDX
*Procedure  

General procedure A (see below) with 4-Methyl-N-(non-4-yn-1-yl)benzenesulfonamide  (1.47 g, 5.0 mmol) and 1-Bromohex-1-yne (886 mg, 5.5 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 4:1) gave the title compound as an orange oil (1.09 g, 59%).

 

General Procedure A:

A solution of the appropriate sulfonamide (1 eq.) and the appropriate bromide (1.1 eq.) in DMF (35 mL) was added to K2CO3 (2 eq.), CuSO4.5H2O (0.1 eq.) and 1,10-phenanthroline (0.2 eq.).  The reaction mixture was stirred at 65 °C 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 water (2 × 100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  59
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp93.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 117i: 4-Methyl-N-(4-(trimethylsilyl)but-3-yn-1-yl)-N-((trimethylsilyl)ethynyl)benzenesulfonamide

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Overall reaction? True
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Attached Files
CSRxnsScheme_117i.cdx
AH Thesis_2011_pp93.pdf
AH Thesis_2011_pp176-223.pdf