反应详情

To 1-(4-Chlorobutyl)-4-methoxybenzene (2468 mg, 12.42 mmol) was added 2-methyl-2-butanol (5 ml), and then 1H-1,2,3-triazole (1286 mg, 18.62 mmol) and potassium iodide (2062 mg, 14.24 mmol) were added. Sodium hydroxide (745 mg, 18.62 mmol) was added and the mixture was refluxed under heating for 4 hours. After cooling to room temperature, toluene and water were added and the mixture was partitioned. The organic layer was washed with water, 20%citric acid (twice), saturated aqueous sodium hydrogen carbonate and water (twice). The organic layer was concentrated under reduced pressure. To the residue was added ethyl acetate and the mixture was concentrated under reduced pressure. Ethyl acetate (20 ml) and isopropyl ether (10 ml) were added and then seed crystal was added. Methanesulfonic acid (1021 mg, 10.62 mmol) was added dropwise while keeping the mixture at 20-30° C. The mixture was stirred at 20-30° C. for 1 hour. The precipitated crystals were collected by filtration and washed with ethyl acetate/isopropyl ether=1/1. The crystals were dried under reduced pressure to give 1-[4-(4-methoxyphenyl)butan-1-yl]-1H-1,2,3-triazole methanesulfonate (3.04 g) as white crystals (yield 75%).

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 4 hours
3. customthe mixture was partitioned
4. washThe organic layer was washed with water, 20%citric acid (twice), saturated aqueous sodium hydrogen carbonate and water (twice)
5. concentrationThe organic layer was concentrated under reduced pressure
6. additionTo the residue was added ethyl acetate
7. concentrationthe mixture was concentrated under reduced pressure
8. additionEthyl acetate (20 ml) and isopropyl ether (10 ml) were added
9. additionseed crystal was added
10. customat 20-30° C
11. filtrationThe precipitated crystals were collected by filtration
12. washwashed with ethyl acetate/isopropyl ether=1/1
13. customThe crystals were dried under reduced pressure