反応 #50422

反応方程式

Potassium t-butoxide

Ethyl formate

2-di-n-propylamino-8-butyryl-1,2,3,4-tetrahydronaphthalene

THF

ammonium hydroxide

Hydroxylamine

tetrahydrofuran

→

2-Di-n-propylamino-8-(4-ethylisoxazol-5-yl)-1,2,3,4-tetrahydronaphthalene

溶媒

water

water

反応条件

後処理

1. 1
   workup.DISSOLUTIONto dissolve the solid
2. 2
   workup.STIRRINGwas stirred at room temperature for 20 hours after which it
3. 3
   抽出The mixture was then extracted with methylene chloride
4. 4
   乾燥The extract was dried over sodium sulfate
5. 5
   その他evaporated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in 100 of toluene, and 100 mg of p-toluenesulfonic acid
7. 7
   workup.ADDITIONwas added
8. 8
   温度The mixture then was refluxed for 1.5 hours after which it
9. 9
   workup.ADDITIONwas poured into water
10. 10
    抽出extracted with methylene chloride
11. 11
    抽出The methylene chloride extract
12. 12
    乾燥was dried over sodium sulfate
13. 13
    その他evaporated

実験手順

Potassium t-butoxide (0.82 g; 7.3 mmol) was suspended in 100 ml of tetrahydrofuran (THF). Ethyl formate (1.0 g; 13.3 mmol) and 2-di-n-propylamino-8-butyryl-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.3 mmol) in THF was added to the mixture. The resulting mixture was stirred at room temperature overnight. Hydroxylamine (1.2 g; 16.6 mmol) was added followed by sufficient water to dissolve the solid. The resulting mixture, having pH 6, was stirred at room temperature for 20 hours after which it was poured into water, and the pH was adjusted to 12 with ammonium hydroxide. The mixture was then extracted with methylene chloride. The extract was dried over sodium sulfate and evaporated. The residue was dissolved in 100 of toluene, and 100 mg of p-toluenesulfonic acid was added. The mixture then was refluxed for 1.5 hours after which it was poured into water and extracted with methylene chloride. The methylene chloride extract was dried over sodium sulfate and evaporated.

出典