反应详情

To a chilled (0° C.) solution of hexaethylene glycol (5.41 g, 19.2 mmol) in DCM (191 mL) were added TsCl (4.02 g, 21.1 mmol), Ag2O (6.67 g, 28.8 mmol), and KI (0.64 g, 3.84 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 33 (6.24 g, 75%): 1H NMR (300 MHz, CDCl3) δ 7.79 (d, J=8.2 Hz, 2H), 7.33 (d, J=8.2 Hz, 2H), 4.23-4.07 (m, 2H), 3.82-3.51 (m, 22H), 2.55 (d, J=6.0 Hz, 1H), 2.44 (s, 3H).

1. filtrationwas filtered through a 4 cm pad of celite
2. customflushed with EtOAc
3. concentrationThe resulted filtrate was concentrated under reduced pressure
4. customto give a yellow oil
5. customThe crude product was purified via silica flash chromatography