Reaktion #165891

Reaktionsgleichung

pentaethylene glycol

TsCl

→

26

Ausbeute 75.1%

14-Hydroxy-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate

Ausbeute 75.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered through a 4 cm pad of celite
2. 2
   Sonstigeflushed with EtOAc
3. 3
   EinengenThe resulted filtrate was concentrated under reduced pressure
4. 4
   Sonstigeto give a yellow oil
5. 5
   SonstigeThe crude product was purified via silica flash chromatography

Vorschrift

To a chilled (0° C.) solution of pentaethylene glycol (2.13 g, 8.92 mmol) in DCM (89 mL) were added TsCl (1.87 g, 9.81 mmol), Ag2O (3.10 g, 0.134 mmol), and KI (0.296 g, 1.78 mmol). After stirring for 20 min the reaction mixture was filtered through a 4 cm pad of celite and flushed with EtOAc. The resulted filtrate was concentrated under reduced pressure to give a yellow oil. The crude product was purified via silica flash chromatography using 3:2 DCM/acetone as an eluent, providing 26 (2.63 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.80 (d, J=8.2 Hz, 2H), 7.34 (d, J=8.2 Hz, 2H), 4.20-4.11 (m, 2H), 3.76-3.54 (m, 18H), 2.44 (s, 3H).

Quelle