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22nd August 2013 @ 10:42

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Reaction information

*#Reaction file  
CSRxnsScheme_134b.cdx
*Reaction file type CDX
*Procedure  TBAF (30 mL of a 1.0 M solution in THF, 30.0 mmol) was added dropwise to a solution of Trimethyl(oct-7-en-1-yn-1-yl)silane  (1.80 g, 10.0 mmol) in THF (20 mL).  The reaction mixture was left stirring at room temperature for 16 h.  The reaction mixture was poured into water (100 mL) and extracted with pentane (2 × 10 mL).  The organic extracts were combined, washed with water (4 × 200 mL), dried (MgSO4) and filtered to give an orange solution. The solution was diluted in dry THF (10.0 mL).  n‑BuLi (3.6 mL of a 2.5 M solution in hexanes, 9.0 mmol) was added dropwise to the reaction mixture at −78 °C.  The reaction mixture was left at room temperature for 30 mins.  1-Tosylaziridine (1.58 g, 8.0 mmol) in dry THF (5 mL) was added dropwise to the reaction mixture at room temperature.  The reaction mixture was left stirring at room temperature for 16 h.  The reaction mixture was poured into a sat. aq. NaHCO3 solution (100 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (2.37 g).  Purification by column chromatography (SiO2, hexane/Et2O 4.5:5.5) gave the title compound as an orange oil (762 mg, 31%).
*Yield (%)  31
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp105.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 134b: N-(Dec-9-en-3-yn-1-yl)-4-methylbenzenesulfonamide

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp105.pdf
CSRxnsScheme_134b.cdx
AH Thesis_2011_pp176-223.pdf