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

HRID 1654200Notes

Reaction equation

HRID 1654200 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C@H: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>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:25])([C@H:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 14978397(3R)-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

Product 1

HCID 10286074(2R,3R)-2-(2,4-Difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediolYield 40.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

In ethanol (50 ml) were dissolved (3R)-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 (4.4 g) and pyridinium p-toluenesulfonate (0.93 g). The solution was stirred for two hours at 55° C. to which was further added pyridinium p-toluenesulfonate (0.20 g), followed by stirring for further two hours at 55° C. The reaction mixture was cooled, then the solvent was distilled off. To the residue was added ethyl acetate (250 ml), which was washed with water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) successively. The ethyl acetate layer was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. To the residue was added ethyl ether, then precipitating crystals were collected by filtration to give (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (1.37 g). m.p. 115°-117° C. [α]D =-80.3° C. (c=1.0 in methanol)

Workup

  1. stirringby stirring for further two hours at 55° C
  2. temperatureThe reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. additionTo the residue was added ethyl acetate (250 ml), which
  5. washwas washed with water (50 ml)
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the residue was added ethyl ether
  9. customprecipitating crystals
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-508de310a21142f2845a92e491210f38
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…