Reacción #1563879

Ecuación de reacción

ammonium hydroxide

2-iodofuran

1-chloro-4-ethynylbenzene

L-proline

Na2CO3

sodium ascorbate

NaN3

→

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

Rendimiento 1.2%

Disolventes

DMSO H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe tube was sealed
2. 2
   Extracciónthe mixture was extracted with ethyl acetate (3×30 ml)
3. 3
   LavadoThe combined organic layers were washed with brine solution (30 ml)
4. 4
   Secadodried over sodium sulfate
5. 5
   Otroevaporated
6. 6
   Otroto yield the crude product, which
7. 7
   Otrowas purified by column chromatography with 20% ethyl acetate/hexane

Procedimiento

A sealed tube was charged sequentially with 2-iodofuran (400 mg, 2.061 mmol), 1-chloro-4-ethynylbenzene (280 mg, 2.061 mmol), L-proline (47.4 mg, 0.412 mmol), Na2CO3 (44 mg, 0.412 mmol), sodium ascorbate (82 mg, 0.412 mmol), DMSO-H2O (9:1; 9 ml), NaN3 (160 mg, 2.47 mmol) and CuSO4.5H2O (514 mg, 2.061 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was then poured into a cold ammonium hydroxide solution, and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were washed with brine solution (30 ml), dried over sodium sulfate, and evaporated to yield the crude product, which was purified by column chromatography with 20% ethyl acetate/hexane to yield 4-(4-chlorophenyl)-1-(furan-2-yl)-1H-1,2,3-triazole (6 mg, 1.2%) as a pale yellow solid. The HPLC purity of the final product was 93.6%. LC-MS [M+1] 246 (C12H8ClN3O+H expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.

Fuente