反応 #1347235

反応方程式

sodium hydroxide

Methyl 4-(benzyloxy)-3-oxobutanoate

azidobenzene

sodium methanolate

→

product

収率 86.7%

5-[(benzyloxy)methyl]-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid

収率 86.7%

溶媒

methanol

反応条件

後処理

1. 1
   温度heated
2. 2
   温度under reflux for 18 hr
3. 3
   温度the mixture was heated
4. 4
   温度under reflux for 2 hr
5. 5
   温度The reaction mixture was cooled to room temperature
6. 6
   濃縮concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue was dissolved in water
8. 8
   洗浄washed with ethyl acetate-hexane (1:1
9. 9
   抽出the mixture was extracted with ethyl acetate
10. 10
    洗浄The extract was washed with saturated brine
11. 11
    乾燥dried over anhydrous magnesium sulfate
12. 12
    その他The solvent was evaporated under reduced pressure

実験手順

Methyl 4-(benzyloxy)-3-oxobutanoate (5.00 g) and azidobenzene (2.68 g) were dissolved in methanol (30 ml), sodium methanolate (28% methanol solution, 6.5 g) was added and the mixture was stirred at room temperature for 2 hr, and then heated under reflux for 18 hr. 1M Aqueous sodium hydroxide solution (10 ml) was added and the mixture was heated under reflux for 2 hr. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in water and washed with ethyl acetate-hexane (1:1, v/v). The obtained aqueous solution was acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (6.03 g).

出典