3-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one → 2-[4-(4-Chloro-phenoxy)-phenylamino]-2-(3-methoxy-phenyl)-ethanol

HRID 1972255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972255
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=4)[CH2:16][O:15]C3=O)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1>[OH-].[Na+].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[CH2:16][OH:15])=[CH:9][CH:8]=2)=[CH:27][CH:28]=1

Komponenten

3

Edukt 1

HCID 687060693-[4-(4-Chlorophenoxy)phenyl]-4-(3-methoxyphenyl)-oxazolidin-2-one

Produkt 1

HCID 687053802-[4-(4-Chloro-phenoxy)-phenylamino]-2-(3-methoxy-phenyl)-ethanolAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23721981Sodium hydroxide methanolLösungsmittel

Versuchsvorschrift

A solution of the product from step 1 (293 mg) in 3 mL of NaOH/MeOH (10%, w/w) is heated to 60° C. for 6 h, then subsequently cooled to room temperature and concentrated. The residue is dissolved in EtOAc (30 ml) and is washed with brine, and dried over MgSO4, filtered, and concentrated to give the crude product, which is by purified flash chromatography on silica gel (EtOAc/Hex: 1/1) to provide 2-[4-(4-chloro-phenoxy)-phenylamino]-2-(3-methoxy-phenyl)-ethanol (202 mg).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in EtOAc (30 ml)
  3. washis washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customby purified flash chromatography on silica gel (EtOAc/Hex: 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-2142ea43e1b642ec975e8240b84f5092
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431607B2

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