Ethyl 4-bromo-3-oxobutanoate → Ethyl 4-hydroxy-3-oxobutanoate

HRID 1719110Notes

Reaction equation

HRID 1719110 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=[O:9])[CH2:7]Br)[CH3:2].C([O-])=[O:12].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6](=[O:9])[CH2:7][OH:12])[CH3:2]

Participants

4

Reactant 2

HCID 575284Ethyl 4-bromo-3-oxobutanoateHCID 2723810Sodium Formate

Product 1

HCID 13335342Ethyl 4-hydroxy-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-3-ketobutyric acid ethyl ester (2a) (21 g, 0.10 moles) in methanol dried prior to use with Molecular Sieves is added sodium formate (10.2 g, 0.15 moles), and the mixture is refluxed for 1 hour. The reaction mixture is concentrated under reduced pressure to remove the solvent. The residue is extracted with chloroform. The extract is purified by silica gel column chromatography (eluting solvent=benzene/ethyl acetate (2:1)) to give the title compound (3a). Yield: 7.34 g, 50%.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customto remove the solvent
  4. extractionThe residue is extracted with chloroform
  5. customThe extract is purified by silica gel column chromatography (eluting solvent=benzene/ethyl acetate (2:1))

Sources & evidence

ORD record
ord-c55309bc81b848f6aa1f6e51d90b2d38
Source dataset
uspto-grants-1985_09
Patent number
US04539148

Reaction notes

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