反応 #165887

反応方程式

16

2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

K2CO3

4-nitrophenol

→

17

収率 94.7%

1-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzene

収率 94.7%

溶媒

DMF

water

反応条件

後処理

1. 1
   温度After cooling
2. 2
   抽出extracted three times with DCM
3. 3
   乾燥dried over MgSO4
4. 4
   濃縮The filtrate was concentrated under reduced pressure
5. 5
   その他to give an oily residue, which
6. 6
   その他was purified by flash chromatography over silica gel with Hex/EtOAc (1:2)

実験手順

To a stirred solution of 16 (1.83 g, 5.75 mmol) in anhydrous DMF (10 mL) were added K2CO3 (2.39 g, 17.3 mmol) and 4-nitrophenol (0.78 g, 5.59 mmol), and the reaction mixture was heated to 80° C. for 16 h. After cooling, the mixture was diluted in water, extracted three times with DCM, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give an oily residue, which was purified by flash chromatography over silica gel with Hex/EtOAc (1:2) to afford 17 as a yellow oil (1.51 g, 92%): 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=9.1 Hz, 2H), 6.97 (d, J=9.1 Hz, 2H), 4.26-3.65 (m, 12H), 3.37 (s, 3H).

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