Water → Methyl 4-cyano-3-oxobutanoate

HRID 1837320Notes

Reaction equation

HRID 1837320 reaction equation
Br[CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[C-:10]#[N:11].[Na+].O>CO>[C:10]([CH2:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6])#[N:11]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 295655Methyl 4-bromo-3-oxobutanoate

Product 1

HCID 9964118Methyl 4-cyano-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

10 g of methyl 4-bromo-3-oxobutanoate is dissolved in 100 g of methanol. The resultant solution is cooled to 0° C. and a solution of 4 g of sodium cyanide in 100 g of methanol is added thereto. After completion of the addition, the mixture is warmed gradually to room temperature under stirring. Thereafter, the reaction mixture is poured into water, and extracted with ethyl acetate. The organic layer is washed with saturated brine, dried, concentrated to obtain methyl 4-cyano-3-oxobutanoate.

Workup

  1. additionAfter completion of the addition
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with saturated brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8160c47d91384ffabfc53baa2984f0a9
Source dataset
uspto-grants-2004_08
Patent number
US06781009B2

Reaction notes

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