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23rd August 2013 @ 09:30

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Reaction information

*#Reaction file
reactionscheme_10 .cdx
*Reaction file type CDX
*Procedure In a 100 mL rbf a solution of 1,4-Didodecyl-2,5-bis(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)-ethynyl)benzene (772 mg, 0.95 mmol) in (3/1) DCM/methanol (40 mL) was stirred in presence of K2CO3 (1.313 g, 9.50 mmol, 10.00 eq.) for 1.5 h. Water was poured in the flask to dissolve the carbonate, then the solution was extracted twice with DCM; the combined organic phases were dried over anhydrous MgSO4 and vacuum evaporated to afford the crude product (pale yellow solid, 635 mg, 0.86 mmol, yield 90%). By NMR the material was assumed to be pure enough for the next step and only a small amount (52 mg) was recrystallized from MeOH yielding a white solid (36 mg) (Rf 0.42, (8/1) hexane/DCM)/
*Yield (%) 90 %
*Type of Yield Reaction yield
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
 
PhD Thesis - 16Sep2010_final p110.pdf
Further information Compound 10: 1-(2-(2,5-Didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene 

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 9: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)-ethynyl)benzene
For step in multistep reaction - link to following reaction step

Reaction 11: Bidirectional Sonogashira Coupling: Synthesis of nitrile functionalised molecular wire: 1,4didodecyl-2,5-bis(2-(4-(2-(4-cyanophenyl)ethynyl)phenyl)ethynyl) benzene

Reaction 12: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-(2-(4-(2-(4-thioacetylphenyl)ethynyl)phenyl)-ethynyl)benzene

Reaction 13: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-bromophenyl)ethynyl)phenyl)ethynyl)-benzene

Attached Files
PhD Thesis - 16Sep2010_final p110.pdf
reactionscheme_10 .cdx