p-Toluenesulfonic acid → 4-(2,3-Difluorophenoxy)-butan-1-ol

HRID 6589

Reaction equation

HRID 6589 reaction equation
[F:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C1COCC1.O>[F:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 220162562-[4-(2,3-Difluorophenoxy)butoxy]-tetrahydropyran

Product 1

HCID 220162574-(2,3-Difluorophenoxy)-butan-1-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

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%)

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane (1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1f6cb91870914577b79f39714d7ce277
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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