Reaktion #6689

Reaktionsgleichung

4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid

4′-(4-Butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid

4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester

DMAP

→

2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyl oxycarbonyl]-phenyl ester

Ausbeute 65.0%

2′,3′-Difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyloxycarbonyl]-phenyl ester

Ausbeute 65.0%

Lösungsmittel

THF

DIC

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with water
2. 2
   Extraktionextracted with ethyl acetate:hexane(1:1)
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification by chromatography on silica gel (5% EtOAc/hexanes)

Vorschrift

To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 2′,3′-difluoro-4′-(4-pentyloxybutoxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethylheptyl oxycarbonyl]-phenyl ester (28) as a white solid (65%).

Quelle