Reacción #6685

Ecuación de reacción

2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran

2-[4-(2,3-Difluorophenoxy)butoxy]-tetrahydropyran

para-toluenesulfonic acid

→

4-(2,3-difluorophenoxy)-butan 1-ol

4-(2,3-Difluorophenoxy)-butan-1-ol

Disolventes

methanol THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with water
2. 2
   Extracciónextracted with ethyl acetate:hexane (1:1)
3. 3
   Lavadowashed with brine
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroPurification by chromatography on silica gel (10% EtOAc/hexanes)

Procedimiento

To a solution of 2-[4-(2,3-difluorophenoxy)-butoxy]-tetrahydropyran (20) (1 equi.) and commercially available para-toluenesulfonic acid (21) (0.1 equi.) in methanol:THF (1:1) (3 mL/mmole), water (0.005 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 (10% EtOAc/hexanes) gave 4-(2,3-difluorophenoxy)-butan 1-ol (22), as a white solid (84%)

Fuente