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21st August 2013 @ 14:04

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Reaction information

*#Reaction file  
CSRxnsScheme_147.cdx
*Reaction file type CDX
*Procedure  Et3N (4.3 mL, 31.1 mmol), DMAP (257 mg, 2.1 mmol) and methane sulfonyl chloride (1.90 mL, 25.0 mmol) were added dropwise sequentially to ((1S,6S)-6-vinylcyclohex-3-en-1-yl)methanol (2.87 g, 20.8 mmol) in dry THF (100 mL) at 0 °C.  The reaction mixture was stirred at 0 °C for 2 h, poured into a sat. aq. NH4Cl solution (200 mL) and extracted with ether (3 × 50 mL).  The organic extracts were combined, washed sequentially with 2 M aq. HCl solution (150 mL), sat. aq. NaHCO3 solution (150 mL) and brine (150 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a yellow oil (4.14 g).  Purification by column chromatography (SiO2, hexane/Et2O 2:1) gave the title compound as a colourless oil (3.95 g, 88%).
*Yield (%)  88
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp224-250.pdf
AH Thesis_2011_pp110.pdf
Further information  Compound 147: ((1S,6S)-6-Vinylcyclohex-3-enyl)methyl methanesulfonate

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_pp110.pdf
CSRxnsScheme_147.cdx
AH Thesis_2011_pp224-250.pdf