Toluene → HCID 67992118, compound

HRID 2358882Notes

Reaction equation

HRID 2358882 reaction equation
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([CH:24]1[CH2:28][CH2:27][C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[C:32]([F:39])[C:31]=2[F:40])(O)[CH2:25]1)[CH2:21][CH2:22][CH3:23]>O>[CH2:20]([CH:24]1[CH2:28][CH2:27][C:26]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[C:32]([F:39])[C:31]=2[F:40])=[CH:25]1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 67992351HCID 67992351, compound

Product 1

HCID 67992118HCID 67992118, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Toluene (50 ml) and p-toluenesulfonic acid monohydrate (0.14 g) were added to 3-butyl-1-(4-ethoxy-2,3-difluorophenyl)cyclopentanol (2.8 g) obtained in the second step, in a reaction vessel equipped with a Dean-Stark apparatus under an atmosphere of nitrogen. The mixture was refluxed for 30 minutes, while forming water was removed with a Dean-Stark apparatus. The reaction solution was cooled to room temperature and was washed with water. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) to give a mixture (2.4 g) of 1-(3-butylcyclopent-1-enyl)-4-ethoxy-2,3-difluorobenzene and 1-(4-butylcyclopent-1-enyl)-4-ethoxy-2,3-difluorobenzene.

Workup

  1. customobtained in the second step, in a reaction vessel
  2. customequipped with a Dean-Stark apparatus under an atmosphere of nitrogen
  3. temperatureThe mixture was refluxed for 30 minutes
  4. customwas removed with a Dean-Stark apparatus
  5. washwas washed with water
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)

Sources & evidence

ORD record
ord-af4b206fa3a14557864839a44f414a5a
Source dataset
uspto-grants-2014_04
Patent number
US08685274B2

Reaction notes

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