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19th August 2013 @ 14:21

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Reaction information

*#Reaction file
reactionscheme_32 .cdx
*Reaction file type CDX
*Procedure In a 250 mL rbf a solution of (2-(trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane  (565 mg, 1.84 mmol) in (5/1) MeOH/DCM (84 mL) was stirred in presence of K2CO3 (2.54 g, 18.4 mmol, 10.0 eq.) for 3 h at r.t. Water was poured in the flask to dissolve the carbonate, then the mixture was extracted with DCM and dried over MgSO4. Evaporation of the solvent afforded the title compound (yellow oil, 380 mg, 1.62 mmol, yield 88%; Rf 0.10 in (10/1) hexane/DCM).
*Yield (%) 88 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p16.pdf
 
PhD Thesis - 16Sep2010_final p123.pdf
Further information Compound 32: (2-(4-Ethynylphenylthio)ethyl)trimethylsilane

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 31: Sonogashira Coupling: (2-(trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane
For step in multistep reaction - link to following reaction step

Reaction 33: Bidirectional Sonogashira Coupling: 1-(2-(trimethylsilyl)ethylthio)-4-(2-(4-(2-(4-(2-(trimethylsilyl)ethylthio)phenyl)ethynyl)-3-nitrophenyl)ethynyl)benzene

Reaction 34: Sonogashira Coupling: 1,4-bis(4-(2-(trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne

Reaction 35: Nucleophilic substitution: (2-(4-(2-(4-bromo-2-nitrophenyl)ethynyl)phenylthio)ethyl)trimethylsilane

Attached Files
reactionscheme_32 .cdx
PhD Thesis - 16Sep2010_final p123.pdf