Reaktion #792203

Reaktionsgleichung

2-bromofuran

phenyl acetylene

L-proline

sodium carbonate

sodium azide

sodium ascorbate

→

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

Ausbeute 5.0%

Lösungsmittel

H2O

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas prepared in a Pierce reaction vessel
2. 2
   SonstigeThe reaction vessel was capped
3. 3
   Extraktionextracted with ethyl acetate (3×30 mL)
4. 4
   ExtraktionThe combined organic extract
5. 5
   Waschenwas then washed with brine (50 mL)
6. 6
   Trocknendried over Na2SO4
7. 7
   Sonstigeevaporated under vacuum
8. 8
   Sonstigepurified through preparative HPLC

Vorschrift

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.

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