Reaktion #52035

Reaktionsgleichung

Difluoro-(4′-methoxy-biphenyl-4-yl)-acetic acid ethyl ester

Diethylaminosulfur trifluoride

(4′-methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester

→

desired product

4,4-Difluoro-4-(4′-methoxy-biphenyl-4-yl)-butyric Acid

Lösungsmittel

Dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   ExtraktionThis mixture is extracted with ethyl acetate twice
3. 3
   TrocknenThe combined organic extracts are dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes)

Vorschrift

Difluoro-(4′-methoxy-biphenyl-4-yl)-acetic acid ethyl ester. Diethylaminosulfur trifluoride (5 mL) is added directly to (4′-methoxy-biphenyl-4-yl)-oxo-acetic acid ethyl ester (3.77 g, 13.3 mmol), prepared as described by Neidlin, et. al., Arzneim.-Forsch. 1983, 33, 691-3. Dichloromethane (2 mL) is added and the mixture is stirred overnight at room temperature. The reaction is diluted with dichloromethane and slowly added to ice water. This mixture is extracted with ethyl acetate twice. The combined organic extracts are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes) to give the desired product as a pale yellow solid.

Quelle