Reaktion #156278

Reaktionsgleichung

ethyl 3-[2-fluoro-4-[[5-(hydroxymethyl)-4-methoxy-2-thienyl]methoxy]phenyl]propanoate

Dess-Martin periodinane

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title compound

Ausbeute 50.8%

Ethyl 3-[2-fluoro-4-[(5-formyl-4-methoxy-2-thienyl)methoxy]phenyl]propanoate

Ausbeute 50.8%

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   Waschenwashed with water (15 mL), brine (15 mL)
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated to dryness
6. 6
   SonstigeThe crude material is purified by silica gel chromatography
7. 7
   Wascheneluting with hexane:ethyl acetate (8.8:1.2)

Vorschrift

To a solution of ethyl 3-[2-fluoro-4-[[5-(hydroxymethyl)-4-methoxy-2-thienyl]methoxy]phenyl]propanoate (1.6 g, 4.3 mmol) in anhydrous dichloromethane (10 mL), cooled to 0° C., is added Dess-Martin periodinane (2.76 g, 6.5 mmol). The reaction mixture is warmed to room temperature and stirred for 2 hours. The reaction mixture is diluted with water (15 mL), extracted with ethyl acetate, washed with water (15 mL), brine (15 mL), dried over sodium sulfate, filtered, and evaporated to dryness. The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (8.8:1.2) to give the title compound (0.8 g, 50%). ESI/MS m/z 367.1 (M+H)+.

Quelle