Anisole → HCID 15264020, compound

HRID 1033738Notes

Reaction equation

HRID 1033738 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:29])([C:16]([S:19]CC1C=CC(OC)=CC=1)([CH3:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:29])([C:16]([SH:19])([CH3:17])[CH3:18])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 20079600HCID 20079600, compound

Product 1

HCID 15264020HCID 15264020, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To 72.0 g (172 mmol) of (+)-2-(2,4-difluoro-phenyl)-3-((4-methoxyphenyl)methylthio)-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol were added 18.6 g (172 mmol) of anisole and 1010 ml of trifluoroacetic acid in this order, followed by stirring at 70° C. for 1.5 hours. After allowing the mixture to cool, the solvent was removed by distillation under reduced pressure, and the residue was neutralized with a saturated sodium hydrogencarbonate aqueous solution, followed by extraction with dichloromethane. The organic layer was washed with a saturated sodium chloride aqueous solution and dried. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography using chloroform as an eluent. The solvent was removed by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and hexane to obtain 44.1 g (86%) of (-)-2-(2,4-difluoro-phenyl)-3-mercapto-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as a colorless crystal.

Workup

  1. temperatureto cool
  2. customthe solvent was removed by distillation under reduced pressure
  3. extractionfollowed by extraction with dichloromethane
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. customdried
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by column chromatography
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was recrystallized from a mixed solvent of isopropyl ether and hexane

Sources & evidence

ORD record
ord-d57fa6bff5cf418e908a29e73dc5ffd6
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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