Ethyl bromoacetate → HCID 86596912, compound

HRID 915189Notes

Reaction equation

HRID 915189 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]([CH:26]([CH3:28])[CH3:27])=[C:12]([CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[CH:19]=2)=[O:17])[N:13]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]([CH:26]([CH3:28])[CH3:27])=[C:12]([CH2:14][CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[C:20]([CH3:25])[CH:19]=2)=[O:17])[N:13]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 12993428HCID 12993428, compound

Product 1

HCID 86596912HCID 86596912, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The synthetic intermediate of Example 1, namely 3-[2-(2,4-dichlorophenyl)-5-isopropyl-4-oxazolyl]-1-(3-methyl-4-hydroxyphenyl)propan-1-one (105 mg, 0.25 mmol) and potassium carbonate (103 mg, 0.75 mmol) were suspended in acetone (3 mL). Ethyl bromoacetate (0.08 mL, 0.75 mmol) was added to the suspension while cooling with ice. The suspension was allowed to room temperature, and refluxed while heating for 6 hours. Insolubles were filtered, and washed with acetone. Subsequently, the solvent was distilled off. The residue was purified by column chromatography on silica gel with hexane/ethyl acetate (7/1-4/1) to give the subject compound (117 mg) as colorless oil (yield 92%)

Workup

  1. temperaturewhile cooling with ice
  2. customwas allowed to room temperature
  3. temperaturerefluxed
  4. temperaturewhile heating for 6 hours
  5. filtrationInsolubles were filtered
  6. washwashed with acetone
  7. distillationSubsequently, the solvent was distilled off
  8. customThe residue was purified by column chromatography on silica gel with hexane/ethyl acetate (7/1-4/1)

Sources & evidence

ORD record
ord-38f87e2f4feb4815b964a5adf5a286f8
Source dataset
uspto-grants-2007_09
Patent number
US07265137B2

Reaction notes

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