Reaction #6691

Reaction equation

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

Solvents

methanol THF

water

Conditions

Workup

1. 1
   Otherquenched with water
2. 2
   Extractionextracted with ethyl acetate:hexane (1:1)
3. 3
   Washwashed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   OtherPurification by chromatography on silica gel (10% EtOAc/hexanes)

Procedure

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%).

Source