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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one

HRID 1654197
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1654197
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[C@H:10]([O:12]C1CCCCO1)[CH3:11].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](=[O:19])[C@H:10]([OH:12])[CH3:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10199305(2R)-1-(2,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

Produkt 1

HCID 9794084(2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-oneAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

In ethanol (3 ml) was dissolved (2R)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (121 mg), to which was added pyridinium p-toluenesulfonate (25 mg), and the mixture was stirred for one hour at 55° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (20 ml). The solution was washed with water and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1) to give (2R)-2',4'-difluoro-2-hydroxypropiophenone (62 mg) as a pale yellow oily product. [α]D +68.7 (c=1.8 in chloroform)

Aufarbeitung

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washThe solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-148157f537fd4a35bacc4db27fa6b91b
Quelldatensatz
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05405861

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