Reaktion #792504

Reaktionsgleichung

(S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

bismuth triflate

→

title compound

Ausbeute 86.0%

(S)-1-chloro-3-(4-(2-(4-((R)-2,3-dihydroxypropoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate

Ausbeute 86.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate
2. 2
   Trocknendried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   SonstigeSolvents were evaporated
5. 5
   Sonstigethe resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane)

Vorschrift

To a solution of crude (S)-1-chloro-3-(4-(2-(4-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)propan-2-yl)phenoxy)propan-2-yl acetate in anhydrous acetonitrile (8.0 mL) was added bismuth triflate (300 mg, 0.46 mmol) in one portion. After 0.5 h, the reaction mixture was partitioned twice with sodium bicarbonate and ethyl acetate. The organic phased were combined, dried over anhydrous magnesium sulfate, and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% to 5% methanol in dichloromethane) to provide the title compound (734 mg, 86%) as a sticky solid.

Quelle