2-[1-[(4-Chlorophenyl)sulfonyl]-3-(2-vinyloxyethoxy)propyl]-1,4-difluorobenzene → 2-[3-[(4-Chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propoxy]ethanol

HRID 748690Notes

Reaction equation

HRID 748690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17]C=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH2:12][CH2:13][O:14][CH2:15][CH2:16][OH:17])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 597507682-[1-[(4-Chlorophenyl)sulfonyl]-3-(2-vinyloxyethoxy)propyl]-1,4-difluorobenzene

Product 1

HCID 597507292-[3-[(4-Chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propoxy]ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 ml) was dissolved 2-[1-[(4-chlorophenyl)sulfonyl]-3-(2-vinyloxyethoxy)propyl]-1,4-difluorobenzene (123 mg, 0.295 mmol). P-toluenesulfonic acid monohydrate (2.0 mg, 0.011 mmol) was added and the mixture was stirred at room temperature for 4 hours. After concentration under reduced pressure, the residue was purified by silica gel chromatography (methylene chloride:methanol=50:1) to yield a white solid. The resulting white solid was washed with hexane, whereby the title compound (80 mg, 70%) was obtained as a white powder.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by silica gel chromatography (methylene chloride:methanol=50:1)
  3. customto yield a white solid
  4. washThe resulting white solid was washed with hexane, whereby the title compound (80 mg, 70%)
  5. customwas obtained as a white powder

Sources & evidence

ORD record
ord-ddf961ecaf9142bcb91b8c033bf69ca0
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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