Anisole → HCID 15264020, compound
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.