Reaction #792187

Reaction equation

trimethyl(thiophen-2-ylethynyl)silane

phenyl azide

1,1,4,7,7-pentamethyldiethlenetriamine

TBAF

→

1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole

Solvents

THF

Conditions

Workup

1. 1
   Otherit was quenched with saturated ammonium chloride solution
2. 2
   Extractionwas extracted with ethyl acetate
3. 3
   WashThe combined organic layers were washed with water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Otherevaporated
6. 6
   OtherThe crude material was purified by column chromatography (100-200 mesh silica gel)

Procedure

To a solution of trimethyl(thiophen-2-ylethynyl)silane (50 mg, 0.2777 mmol), phenyl azide (0.5 M solution, 1.1 ml, 0.555 mmol), and CuI (52.87 mg, 0.2777 mmol) in THF (1 ml) was added 1,1,4,7,7-pentamethyldiethlenetriamine (0.116 ml, 0.555 mmol) and 1M TBAF.3H2O (0.554 ml, 0.554 mmol). After stirring the reaction mixture for 20 hours at room temperature, it was quenched with saturated ammonium chloride solution and was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using 5% ethyl acetate in hexane as eluant to yield 1-phenyl-4-(thiophen-2-yl)-1H-1,2,3-triazole (30 mg, 0.132 mol, yield 47.61%) with an HPLC purity of 97.64%. LC-MS [M+H] 228.2 (C12H9N3S+H, expected 228.05). The 1H-NMR spectra was in accordance with the chemical structure.

Source