反应 #6695

反应方程式

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

[R]-1-Trifluoromethylheptyl 4-Benzyloxybenzoate

DMAP

→

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

收率 65.0%

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

收率 65.0%

溶剂

THF

DIC

反应条件

后处理

1. 1
   其他quenched with water
2. 2
   萃取extracted with ethyl acetate:hexane(1:1)
3. 3
   洗涤washed with brine
4. 4
   干燥dried over MgSO4
5. 5
   浓缩concentrated in vacuo
6. 6
   其他Purification by chromatography on silica gel (5% EtOAc/hexanes)

实验过程

To a solution of 4′-(4-butoxybutoxy)-2′,3′-difluorobiphenyl-4-carboxylic acid (27) (1 equi.), (4-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl ester (13, Scheme 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-trifluoromethylheptyloxycarbonyl]-phenyl ester (28) as a white solid (65%).

来源