Ethyl bromoacetate → HCID 11287642, compound

HRID 2056265Notes

Reaction equation

HRID 2056265 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[CH3:10][O:9][C:7]([C:5]1[O:4][N:3]=[C:2]([O:1][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:6]=1)=[O:8]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178498603HCID 178498603, compound

Product 1

HCID 11287642HCID 11287642, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 3-hydroxy-isoxazole-5-carboxylate (7.14 mmol) in acetone (30 mL), was added potassium carbonate (1.2 g, 8.6 mmol) and ethyl bromoacetate (8.6 mmol). The reaction mixture was heated at reflux for 2 h, monitoring by TLC. At completion, acetone was removed in vacuo and the residue partitioned between water and ethyl acetate (50 mL). The organic layer was dried (MgSO4), filtered, and evaporated to afford the desired intermediate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customAt completion, acetone was removed in vacuo
  4. customthe residue partitioned between water and ethyl acetate (50 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-82811266ae484c7f923d9f075aa82098
Source dataset
uspto-grants-2008_02
Patent number
US07335655B2

Reaction notes

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