Reaktion #165887

Reaktionsgleichung

16

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

K2CO3

4-nitrophenol

→

17

Ausbeute 94.7%

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

Ausbeute 94.7%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionextracted three times with DCM
3. 3
   Trocknendried over MgSO4
4. 4
   EinengenThe filtrate was concentrated under reduced pressure
5. 5
   Sonstigeto give an oily residue, which
6. 6
   Sonstigewas purified by flash chromatography over silica gel with Hex/EtOAc (1:2)

Vorschrift

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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