Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2RS,3RS)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol

HRID 1654185Notes

Reaction equation

HRID 1654185 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([O:18]C1CCCCO1)[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([CH:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 200796062-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol

Product 1

HCID 14706433(2RS,3RS)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediolYield 99%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

In ethanol (500 ml) was dissolved 2-(2,4-difluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yl)oxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol (51.4 g), to which was added pyridinium p-toluenesulfonate (13.2 g), and the mixture was stirred for 6 hours at 55° C. To the resultant mixture was further added pyridinium p-toluenesulfonate (2.0 g), which was stirred for 1.5 hour at 55° C. The mixture was cooled, then the solvent was distilled off under reduced pressure. To the residue was added ethyl acetate (900 ml), and the mixture was washed with water (50 ml) three times. The ethyl acetate layer was dried over anhydrous magnesium suflate, then the solvent was distilled off. To the residue were added ethyl acetate (50 ml) and ethyl ether (100 ml). Precipitating crystals were collected by filtration to afford pure (99% purity) (2RS,3RS)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (29.0 g) as diastereomer, m.p. 154°-156° C.

Workup

  1. stirringwas stirred for 1.5 hour at 55° C
  2. temperatureThe mixture was cooled
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionTo the residue was added ethyl acetate (900 ml)
  5. washthe mixture was washed with water (50 ml) three times
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium suflate
  7. distillationthe solvent was distilled off
  8. additionTo the residue were added ethyl acetate (50 ml) and ethyl ether (100 ml)
  9. customPrecipitating crystals
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-da5a8ee74648427795f2c9e40bac4a95
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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