Ethylene carbonate → [3,5-Dichloro-4-(2-hydroxy-ethoxy)-phenyl]-carbamic acid tert-butyl ester

HRID 649850Notes

Reaction equation

HRID 649850 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([OH:15])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].C1(=O)O[CH2:27][CH2:26][O:25]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[C:11]([O:15][CH2:27][CH2:26][OH:25])=[C:10]([Cl:16])[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 22048528(3,5-Dichloro-4-hydroxy-phenyl)-carbamic Acid Tert-butyl Ester

Product 1

HCID 54068949[3,5-Dichloro-4-(2-hydroxy-ethoxy)-phenyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (3,5-dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester (1.0 g) and potassium carbonate (0.55 g) in toluene (20 mL) is added ethylene carbonate (1.6 g) and the mixture is heated to reflux for 3 hours. To the cooled reaction mixture is added 2.5 M aqueous sodium hydroxide (50 mL), and the separated organic layer is then washed successively with water, then saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. The solvent is then removed by evaporation under reduced pressure and the resulting residue is chromatographed over silica gel (30% ethyl acetate in hexanes is used as the eluant) to provide the desired product as a white foam.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 3 hours
  3. customTo the cooled reaction mixture
  4. washthe separated organic layer is then washed successively with water
  5. dry with materialsaturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate
  6. customThe solvent is then removed by evaporation under reduced pressure
  7. customthe resulting residue is chromatographed over silica gel (30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7f3aca0f81d74114a9d8a1389b35c9a1
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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