Reacción #58668

Ecuación de reacción

1-(3,5-difluorophenyl)cyclopentanecarboxylic acid methyl ester

potassium hydroxide

→

title compound

1-(3,5-Difluorophenyl)cyclopentanecarboxylic acid

Disolventes

dimethylsulfoxide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction mixture was partitioned between ether (50 mL) and saturated aqueous hydrochloric acid (2 N, 50 mL)
2. 2
   OtroThe organic layer was separated
3. 3
   Extracciónthe aqueous layer extracted with ether (2×50 mL)
4. 4
   SecadoThe combined extracts were dried over anhydrous sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated to dryness

Procedimiento

To a solution of 1-(3,5-difluorophenyl)cyclopentanecarboxylic acid methyl ester (Step A, 2.0 g, 8.3 mmol) in dimethylsulfoxide (5 mL) was added potassium hydroxide (1.9 g, 33 mol) in 2 mL of water. After stirring at room temperature for 2.5 h, the reaction mixture was partitioned between ether (50 mL) and saturated aqueous hydrochloric acid (2 N, 50 mL). The organic layer was separated and the aqueous layer extracted with ether (2×50 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound. 1H NMR (400 MHz, CD3OD): δ 6.97 (m, 2H), 6.80 (m. 1H), 2.60 (m, 2H), 1.84 (m, 2H), 1.74 (m, 4H).

Fuente