p-Toluenesulfonic acid monohydrate → 5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-1-pentanol

HRID 748684Notes

Reaction equation

HRID 748684 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH2:12][CH2:13][CH2:14][CH2:15][O:16]C=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH2:12][CH2:13][CH2:14][CH2:15][OH:16])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 597507152-[1-[(4-Chlorophenyl)sulfonyl]-5-vinyloxypentyl]-1,4-difluorobenzene

Product 1

HCID 597508325-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)-1-pentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (30 ml) was dissolved 2-[1-[(4-chlorophenyl)sulfonyl]-5-vinyloxypentyl]-1,4-difluorobenzene (0.90 g, 2.3 mmol). After addition of p-toluenesulfonic acid monohydrate (20 mg, 0.11 mmol), the resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2) to yield a white solid. The resulting white solid was washed with diisopropyl ether, whereby the title compound (0.73 g, 85%) was obtained as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:2)
  3. customto yield a white solid
  4. washThe resulting white solid was washed with diisopropyl ether, whereby the title compound (0.73 g, 85%)
  5. customwas obtained as a white powder

Sources & evidence

ORD record
ord-ad56676787b641fbbf100e5d24e299b5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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