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22nd August 2013 @ 09:35

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Reaction information

*#Reaction file  
CSRxnScheme_200.cdx
*Reaction file type CDX
*Procedure  Et3N (0.23 mL, 1.7 mmol) and methane sulfonyl chloride (0.08 mL, 1.2 mmol) were added dropwise to 1-(Trimethylsilyl)trideca-1,8-diyn-5-ol  (287 mg, 1.1 mmol) in dry DCM (2.0 mL) at −20 °C.  The reaction mixture was stirred at −20 °C for 45 mins and at room temperature for 2 h.  The reaction mixture was poured into 2 M aq. HCl solution (30 mL).  The aqueous layer was further extracted with DCM (30 mL).  The organic extracts were combined, washed with water (2 × 30 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (327 mg, 87%).
*Yield (%)  87
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp152-200.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 200: 1-(Trimethylsilyl)trideca-1,8-diyn-5-yl mesylate

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Overall reaction? True
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Attached Files
CSRxnScheme_200.cdx
AH Thesis_2011_pp145-167.pdf
AH Thesis_2011_pp152-200.pdf