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20th August 2013 @ 11:28

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Reaction information

*#Reaction file
reactionscheme_39 .cdx
*Reaction file type CDX
*Procedure In a 1 L rbf, compound trimethyl(2-(4-(methylthio)phenyl)ethynyl)silane (2.11 g, 9.57 mmol) was dissolved in MeOH (300 mL) and stirred for 0.5 h in presence of K2CO3 (13.21 g, 95.58 mmol, 9.99 eq.). Water (300 mL) was poured in the flask and the mixture was extracted with DCM (2 x 250 mL); the combined organic phase was washed with water and brine, and dried over MgSO4. Evaporation of the solvent afforded the pure title compound (GC, SD_FASTD, RT 3.6 minutes; Rf 0.20 in (20/1) hexane/DCM) as a brownish oil (1.375 g, 9.28 mmol, yield 97 %) with a characteristic scent of mushroom.
*Yield (%) 97 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p19.pdf
 
PhD Thesis - 16Sep2010_final p128.pdf
Further information Compound 39: (4-Ethynylphenyl)(methyl)sulfane

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step Reaction 21: Sonogashira Coupling: Trimethyl(2-(4-(methylthio)phenyl)ethynyl)silane
For step in multistep reaction - link to following reaction step Reaction 42: Sonogashira coupling: 2,5-bis(2-(4-(methylthio)phenyl)ethynyl)benzoic acid
Attached Files
PhD Thesis - 16Sep2010_final p19.pdf
PhD Thesis - 16Sep2010_final p128.pdf
reactionscheme_39 .cdx