反応 #1271445

反応方程式

sodium hydride

methyl 7-methoxy-3-oxoheptanoate

Phenyl azide

→

product

収率 52.4%

5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid

収率 52.4%

溶媒

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 15 hr
2. 2
   濃縮The solvent was concentrated under reduced pressure, and methanol (100 ml)
3. 3
   workup.ADDITIONwas added to the residue and 4N aqueous sodium hydroxide solution (20 ml)
4. 4
   workup.ADDITIONwas further added
5. 5
   workup.STIRRINGThe mixture was stirred at 60° C. for 1 hr
6. 6
   その他The solvent was evaporated under reduced pressure and water (100 ml)
7. 7
   workup.ADDITIONwas added to the residue
8. 8
   workup.ADDITION6N Hydrochloric acid was added for neutralization
9. 9
   抽出the mixture was extracted with ethyl acetate (100 ml×2)
10. 10
    乾燥The extract was dried over anhydrous sodium sulfate
11. 11
    その他the solvent was evaporated under reduced pressure
12. 12
    洗浄a fraction eluted with ethyl acetate
13. 13
    濃縮was concentrated under reduced pressure

実験手順

A solution of sodium hydride (60% in oil, 2 g) in DMF (50 ml) was cooled to 0° C.-5° C., methyl 7-methoxy-3-oxoheptanoate (9.4 g) was added, and the mixture was stirred at 0° C.-5° C. for 30 min. Phenyl azide (6 g) was added, and the mixture was stirred at room temperature for 15 hr. The solvent was concentrated under reduced pressure, and methanol (100 ml) was added to the residue and 4N aqueous sodium hydroxide solution (20 ml) was further added. The mixture was stirred at 60° C. for 1 hr. The solvent was evaporated under reduced pressure and water (100 ml) was added to the residue. 6N Hydrochloric acid was added for neutralization and the mixture was extracted with ethyl acetate (100 ml×2). The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (7.2 g) as a white powder.

出典