Methyl iodide → 5-methyl-1-(4-vinylphenyl)-1H-1,2,4-triazole

To a stirred solution of 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (0.5 g, 2.9 mmol) in 10 mL of THF, was added n-BuLi (0.22 g, 3.5 mmol) at −78° C. and stirred for 30 min. To this methyl iodide in THF (0.50 g, 3.5 mmol) was added and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with a saturated aqueous NH4Cl solution and extracted with EtOAc (3×25 mL). The combined EtOAc layer was washed with brine and dried over sodium sulphate and concentrated under reduced pressure The crude compound was purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether) afford the title compound as a pale brown liquid (250 mg, 46%): 1H NMR (400 MHz, CDCl3) δ 7.93 (s, 1H), 7.55 (d, J=9 Hz, 2H), 7.42 (d, J=9 Hz, 2H), 6.76 (dd, J=18, 11 Hz, 1H), 5.83 (d, J=18 Hz, 1H), 5.38 (d, J=11 Hz, 1H), 2.55 (s, 3H); ESIMS m/z 186.13 ([M+H]+); IR (thin film) 1517, 1386, 1182, 847 cm−1.

1. customthe resultant reaction mixture
2. stirringwas stirred at RT for 16 h
3. customThe reaction mixture was quenched with a saturated aqueous NH4Cl solution
4. extractionextracted with EtOAc (3×25 mL)
5. washThe combined EtOAc layer was washed with brine
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated under reduced pressure The crude compound
8. customwas purified by flash chromatography (SiO2, 100-200 mesh, 40% EtOAc in Pet ether)

ORD record

ord-1b89dc22b8f84af28442e7c18e13dc0c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09212163B2