Réaction #792203

Équation de réaction

2-bromofuran

phenyl acetylene

L-proline

sodium carbonate

sodium azide

sodium ascorbate

→

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

Rendement 5.0%

Solvants

H2O

DMSO

Conditions de réaction

Traitement

1. 1
   Autrewas prepared in a Pierce reaction vessel
2. 2
   AutreThe reaction vessel was capped
3. 3
   Extractionextracted with ethyl acetate (3×30 mL)
4. 4
   ExtractionThe combined organic extract
5. 5
   Lavagewas then washed with brine (50 mL)
6. 6
   Séchagedried over Na2SO4
7. 7
   Autreevaporated under vacuum
8. 8
   Autrepurified through preparative HPLC

Mode opératoire

A stirred solution of 2-bromofuran (500 mg, 3.40 mmol) and phenyl acetylene (347 mg, 3.39 mmol) in a mixture of solvents (9:1 DMSO:H2O, 4 mL) was prepared in a Pierce reaction vessel. L-proline (78 mg, 0.68 mmol), sodium carbonate (72 mg, 0.68 mmol), sodium azide (265 mg, 4.07 mmol), copper sulfate, pentahydrate (43 mg, 0.17 mmol), and sodium ascorbate (67 mg, 0.34 mmol), respectively, were then added to the vessel. The reaction vessel was capped and the mixture was heated at 65° C. for 18 hours. The reaction mass was poured into 50 mL of ice-water, stirred for 10 minutes, and extracted with ethyl acetate (3×30 mL). The combined organic extract was then washed with brine (50 mL), dried over Na2SO4, and evaporated under vacuum. The resulting crude compound was auto purified through preparative HPLC to yield the desired 1-(furan-2-yl)-4-phenyl-1H-1,2,3-triazole (36 mg, 5%) as a light yellow solid. The melting point of the final product was determined to be 99-101° C. The HPLC purity of the final product was 95.34%. LC-MS [M+1]212 (C12H9N3O+H expected 212.07). The 1H-NMR spectra was in accordance with the chemical structure.

Source