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 1654185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654185
[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

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-da5a8ee74648427795f2c9e40bac4a95
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405861

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