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

HRID 1464201

Reaction equation

HRID 1464201 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-93da1b7258ff420b8a22da77c0757bc0
Source dataset
uspto-grants-1994_04
Patent number
US05302739

Linked notes

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