Ethyl bromoacetate → HCID 136342999, compound

HRID 915191Notes

Reaction equation

HRID 915191 reaction equation
[OH: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>[C:37]([O:39][CH2:40][CH2:41][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][CH2:14][C:12]2[N:13]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[OH:1])[O:10][C:11]=2[CH:26]([CH3:28])[CH3:27])=[CH:19][C:20]=1[CH3:25])(=[O:38])[CH3:36]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 136342974HCID 136342974, compound

Product 1

HCID 136342999HCID 136342999, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The obtained 3-[2-(2-hydroxy-4-chlorophenyl)-5-isopropyl-4-oxazolyl]-1-(3-methyl-4-hydroxyphenyl)propan-1-one (378 mg, 0.95 mmol) was dissolved in acetone (20 mL). To the solution, potassium carbonate (158 mg, 0.95 mmol) and ethyl bromoacetate (158 mg, 0.95 mmol) were added while cooling with ice. The mixture was allowed to room temperature, and stirred for 20 hours. After insoluble was filtered off, the mixture was washed with acetone to remove the solvent. The residue was purified by column chromatography on silica gel with hexane/ethyl acetate (4/1) to give the desired compound (315 mg) as white solid (yield 69%).

Workup

  1. temperaturewhile cooling with ice
  2. customwas allowed to room temperature
  3. filtrationAfter insoluble was filtered off
  4. washthe mixture was washed with acetone
  5. customto remove the solvent
  6. customThe residue was purified by column chromatography on silica gel with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record
ord-bd44470de1644ddf9a88b2e4127dfbcb
Source dataset
uspto-grants-2007_09
Patent number
US07265137B2

Reaction notes

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