反応 #331480

反応方程式

NaHSO3

Florisil

compound

4,5-dibromo-1-cyclohexene

N-methylmorpholine

→

4,5-dibromo-1,2-cyclohexanediol

溶媒

water

water

acetone

反応条件

後処理

1. 1
   workup.STIRRINGwas vigorously stirred for 24 hours
2. 2
   その他After the completion of the reaction
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   workup.STIRRINGwas stirred for 10 minutes
5. 5
   その他After that, insoluble matter was removed by celite filtration, and 5% HCl
6. 6
   workup.ADDITIONwas added to the filtrate until the pH of the filtrate
7. 7
   その他was removed under reduced pressure
8. 8
   抽出Organic matter was extracted from the remainder with ethyl acetate
9. 9
   乾燥dried over sodium sulfate
10. 10
    濃縮concentrated under reduced pressure
11. 11
    ろ過The precipitated crystals were filtrated
12. 12
    その他was then recrystallized with methylene chloride

実験手順

The compound obtained in Step (9) (80.5 g, 338 mmol), water (500 ml), acetone (250 ml), and N-methylmorpholine (45.5 g, 389 mmol) were placed in a reaction vessel, and was stirred. OsO4 (1 g) was added to the mixture, and was vigorously stirred for 24 hours. After the completion of the reaction, a suspension of NaHSO3 (50 g) and Florisil (250 g) in water (100 ml) was added to the reaction solution, and was stirred for 10 minutes. After that, insoluble matter was removed by celite filtration, and 5% HCl was added to the filtrate until the pH of the filtrate became 3. Upon confirming that the pH had reached 3, and acetone was removed under reduced pressure. Organic matter was extracted from the remainder with ethyl acetate, dried over sodium sulfate, and concentrated under reduced pressure. The precipitated crystals were filtrated, and was then recrystallized with methylene chloride, whereby 4,5-dibromo-1,2-cyclohexanediol was obtained (64.6 g, 70%).

出典