Reaction #1563865

Reaction equation

ammonium hydroxide

2-ethynylfuran

1-chloro-4-iodobenzene

L-proline

Na2CO3

sodium ascorbate

NaN3

→

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

Yield 4.9%

Solvents

DMSO H2O

Conditions

Workup

1. 1
   OtherThe tube was sealed
2. 2
   Extractionthe mixture was extracted with ethyl acetate (3×30 ml)
3. 3
   WashThe combined organic layers were washed with brine solution (30 ml)
4. 4
   Dryingdried over sodium sulfate
5. 5
   Otherevaporated
6. 6
   Otherto yield the crude material, which
7. 7
   Otherwas purified by column chromatography with 20% ethyl acetate/hexane

Procedure

A sealed tube was charged sequentially with 2-ethynylfuran (153 mg, 1.663 mmol), 1-chloro-4-iodobenzene (395 mg, 1.663 mmol), L-proline (38.2 mg, 0.332 mmol), Na2CO3 (35 mg, 0.332 mmol), sodium ascorbate (66 mg, 0.332 mmol), DMSO-H2O (9:1; 7 ml), NaN3 (130 mg, 1.99 mmol) and CuSO4.5H2O (415 mg, 1.663 mmol). The tube was sealed and stirred at 65° C. for 16 hours. The reaction mixture was poured onto 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 material, which was purified by column chromatography with 20% ethyl acetate/hexane yielding 1-(4-chlorophenyl)-4-(furan-2-yl)-1H-1,2,3-triazole (20 mg, yield 4.9%) as a pale yellow solid. The HPLC purity was 98.02%. LC-MS [M+H] 246 (C12H8ClN3O+H, expected 246.04). The 1H-NMR spectra was in accordance with the chemical structure.

Source