反応 #1271449

反応方程式

sodium hydroxide

azidobenzene

sodium methoxide methanol

ethyl 3-oxo-5-phenylpentanoate

→

product

収率 32.8%

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

収率 32.8%

溶媒

methanol

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at 60° C. for 1 hr
2. 2
   その他The solvent was evaporated under reduced pressure and water (20 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   workup.ADDITION1N Hydrochloric acid was added for neutralization
5. 5
   抽出the mixture was extracted with ethyl acetate (30 ml×2)
6. 6
   乾燥The extract was dried over anhydrous sodium sulfate
7. 7
   その他the solvent was evaporated under reduced pressure
8. 8
   洗浄a fraction eluted with ethyl acetate
9. 9
   濃縮was concentrated under reduced pressure

実験手順

A solution of ethyl 3-oxo-5-phenylpentanoate (1.1 g) in methanol (50 ml) was cooled to 0° C.-5° C., azidobenzene (600 mg) and 28% sodium methoxide methanol solution (965 mg) were added and the mixture was stirred at 60° C. for 3 hr. Then, 1N sodium hydroxide (10 ml) was added and the mixture was stirred at 60° C. for 1 hr. The solvent was evaporated under reduced pressure and water (20 ml) was added. 1N Hydrochloric acid was added for neutralization and the mixture was extracted with ethyl acetate (30 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 (480 mg) as a powder.

出典