反応 #2508990

反応方程式

1-Tosyloxy-3,6,9-trioxadecane

2,7-dibromofluorene

Sodium hydride

→

2,7-dibromo-9,9-bis(3,6,9-trioxadecyl)fluorene

収率 60.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   温度refluxed for 5 hours
2. 2
   温度to refluxed over night
3. 3
   温度cooled down
4. 4
   workup.ADDITIONpoured
5. 5
   workup.DISTILLATIONinto distill water
6. 6
   抽出extracted with chloroform (2×100 mL)
7. 7
   洗浄The combined organic solutions were washed with saturated NaCI solution (2×100 mL)
8. 8
   workup.DISTILLATIONdistilled water (1×100 mL)
9. 9
   乾燥dried over MgSO4
10. 10
    濃縮concentrated under reduced pressure
11. 11
    その他Crude oil was further purified by column chromatography
12. 12
    その他The fraction at Rf=0.12 was collected
13. 13
    濃縮concentrated
14. 14
    その他to give 5.7 product in 60% yield

実験手順

2,7-dibromofluorene (5.0 g, 15.4 mmol) was dissolved in dried THF solution (30 mL). Sodium hydride (1.0 g, 40 mmol) was added to the THF solution at room temperature and refluxed for 5 hours. 1-Tosyloxy-3,6,9-trioxadecane (11.8 g, 37 mmol) in 20 mL of dry THF was added drop-wise to the refluxed solution. The mixture was allowed to refluxed over night, then cooled down, poured into distill water and extracted with chloroform (2×100 mL). The combined organic solutions were washed with saturated NaCI solution (2×100 mL), distilled water (1×100 mL), dried over MgSO4, and concentrated under reduced pressure. Crude oil was further purified by column chromatography using hexane/ethyl acetate (50/50) as eluant. TLC (ethyl acetate/Hexane=1/1) Rf =0.12. The fraction at Rf=0.12 was collected and concentrated to give 5.7 product in 60% yield. 1H NMR (300 MHz, CDCl3), 2.34(t, 4H), 2.77(t, 4H), 3.10-3.60(m, 22H), 7.40-7.60(m, 6H).

出典