Water → Tert-butyl 2-acetoxyacetoacetate

HRID 130373Notes

Reaction equation

HRID 130373 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Br[CH:7]([C:15]([CH3:17])=[O:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O>CN(C=O)C>[C:1]([O:4][CH:7]([C:15]([CH3:17])=[O:16])[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 108899382-Bromo-3-oxobutyric acid tert-butyl ester

Product 1

HCID 11736056Tert-butyl 2-acetoxyacetoacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium acetate (30.76 g, 375 mmol) in DMF (250 mL) was added dropwise tert-Butyl 2-bromo-acetoacetate (59.27 g, 250 mmol). After stirring at ambient temperature for 90 minutes, water (415 mL) was added, followed by extraction with ethyl acetate (3×325 mL). The combined organic layers were washed with water (3×325 mL) and brine (325 mL), dried over Na2SO4 and after filtration, the solvent was removed in vacuo. The resulting oil was purified by distillation (12 mbar, 128°)

Workup

  1. extractionfollowed by extraction with ethyl acetate (3×325 mL)
  2. washThe combined organic layers were washed with water (3×325 mL) and brine (325 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationafter filtration
  5. customthe solvent was removed in vacuo
  6. distillationThe resulting oil was purified by distillation (12 mbar, 128°)

Sources & evidence

ORD record
ord-015bf827b7404fa9818d5a669b2c4b44
Source dataset
uspto-grants-2008_06
Patent number
US07381743B2

Reaction notes

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