Реакция #52035

Уравнение реакции

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

Растворители

Dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеprepared
2. 2
   ЭкстракцияThis mixture is extracted with ethyl acetate twice
3. 3
   СушкаThe combined organic extracts are dried over Na2SO4
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe crude product is purified by column chromatography (silica gel, 5% EtOAc/hexanes)

Методика

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.

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