Ethyl 2-bromopropionate → Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[(1-ethoxycarbonylethyl)oxyiminomethyl)benzoate

HRID 4906

Reaction equation

HRID 4906 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[N:23][OH:24])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:4]=1.Br[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>[Ag]=O.CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=[N:23][O:24][CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:32])[C:13]=2[C:14]([O:16][CH3:17])=[O:15])[N:4]=1

Participants

5

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 86747184Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate

Product 1

HCID 86747185Methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[(1-ethoxycarbonylethyl)oxyiminomethyl)benzoateYield 27%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Procedure

2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate, 3 ml of ethyl 2-bromopropionate and 0.9 g of silver oxide (I) were place in a 50 ml eggplant type flask, and were allowed to stand for one night at room temperature. 10 ml of acetone and 10 g of silica gel were added to the resultant reaction liquor, and the acetone was distilled off under reduced pressure. The resultant product was purified by column chromatography to obtain 0.7 g of the aimed compound (refractive index=1.5261) at a yield of 27%.

Workup

  1. waitto stand for one night at room temperature
  2. customreaction liquor
  3. distillationthe acetone was distilled off under reduced pressure
  4. customThe resultant product was purified by column chromatography

Sources & evidence

ORD record
ord-58d146d694ce48609c737e896ac57533
Source dataset
uspto-grants-1993_09
Patent number
US05242895

Linked notes

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