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

HRID 1972255Notes

Reaction equation

HRID 1972255 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 687053802-[4-(4-Chloro-phenoxy)-phenylamino]-2-(3-methoxy-phenyl)-ethanolYield 73.8%

Reagents, catalysts & solvents 1

HCID 23721981Sodium hydroxide methanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2142ea43e1b642ec975e8240b84f5092
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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