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ChemicalBook CAS DataBase List 4'-DIMETHYLAMINOPHENYL ACETYLENE
17573-94-3

4'-DIMETHYLAMINOPHENYL ACETYLENE synthesis

13synthesis methods
-

Yield: 99%

Reaction Conditions:

with potassium carbonate in methanol at 20; for 3 h;

Steps:

4.3 Typical procedure for the preparation of N-(4-ethynylphenyl)carbazole (5a)
General procedure: 9-[4-{2-(Trimethylsilyl)ethynyl}phenyl]carbazole (4a, 0.68g, 2.7mmol), potassium carbonate (0.42g, 3.0mmol), and methanol (4.0mL) were placed in a flask, and the suspension was stirred at room temperature. After stirring for 3h, the precipitate that was insoluble in the solvent was separated by atmospheric filtration, and the filtrate was poured into saturated aqueous NH4Cl solution (20mL). The crude product was extracted with AcOEt (20mL) three times and the combined organic layer was washed with brine (once). The organic layer was collected and dried over anhydrous Na2SO4, which was separated by filtration. The filtrate was evaporated in vacuo and subjected to silica-gel column chromatography (eluent: hexane/CH2Cl2=5/1) to obtain the deprotection product 5a in 99% yield (0.53g, 2.0mmol) as a white solid.

References:

Yamada, Shigeyuki;Morita, Masato;Konno, Tsutomu [Journal of Fluorine Chemistry,2017,vol. 202,p. 54 - 64]

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