Hydrochloric Acid → (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 1077890

Reaktionsgleichung

Reaktionsgleichung von HRID 1077890
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([O:14]C(=O)C2C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=2)[CH3:13])[CH2:11][O:10]1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10691998[(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate

Produkt 1

HCID 10536015(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanolAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

[(1R )-1-[(2R )-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate (50 g) was dissolved in two liters of methanol and, at room temperature, 255 ml of 1N sodium hydroxide was added dropwise thereinto. The reaction solution was stirred at room temperature for one hour and neutralized with 127 ml of 1N hydrochloric acid. Methanol was distilled off under reduced pressure, then one liter of ethyl acetate and 200 ml of water were added to the residue, and the mixture was extracted with ethyl acetate. The organic extract was washed with 200 ml of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/3) to give 25 g of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol as a pale yellow oil.

Aufarbeitung

  1. distillationMethanol was distilled off under reduced pressure
  2. additionone liter of ethyl acetate and 200 ml of water were added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with 200 ml of a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationdistilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=1/3)

Quellen und Nachweise

ORD-Eintrag
ord-2d55366507134617b4e443f2aa26acc6
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05545652

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