Ethyl bromopyruvate → HCID 59457496, compound

HRID 1710750Notes

Reaction equation

HRID 1710750 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1.Br[CH2:16][C:17](=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(#N)CC>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]2[O:11][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:12]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 59457496HCID 59457496, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

A mixture of 4-(3-chloropropoxy)benzamide ax54 (3.55 g, 16.6 mmol, 1 eq) and ethyl bromopyruvate (3.24 g, 16.6 mmol, 1 eq) in propionitrile (60 ml) is heated at reflux. After 24 h, the solvent is evaporated, and the residue is taken up in ethyl acetate and washed two times with an aqueous solution of sodium hydrogenocarbonate. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum. Purification by chromatography over silicagel (eluent: dichloromethane/hexane 90:10) affords 2.12 g of ethyl 2-[4-(3-chloropropoxy)phenyl]-1,3-oxazole-4-carboxylate i33.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. customthe solvent is evaporated
  4. washwashed two times with an aqueous solution of sodium hydrogenocarbonate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification by chromatography over silicagel (eluent: dichloromethane/hexane 90:10)

Sources & evidence

ORD record
ord-69892472dc9948828179cc8ade6f523e
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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