Acetic Acid → Ethyl 4-cyano-2-oxobutanoate

HRID 962402Notes

Reaction equation

HRID 962402 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:13])(P(O)(O)=O)[C:6]([OH:8])=[O:7].[C-]#N.[K+].[C:17](O)(=O)[CH3:18]>C(O)C.O>[C:2]([CH2:3][CH2:4][C:5](=[O:13])[C:6]([O:8][CH2:17][CH3:18])=[O:7])#[N:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 19084823HCID 19084823, compound

Product 1

HCID 15089956Ethyl 4-cyano-2-oxobutanoate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 12.8 g (0.10 mole) of ethyl 2-oxo-3-butenoic acid (prepared as in Example 1) in 100 ml of ethanol and 50 ml of water is added 6.5 g (0.10 mole) of potassium cyanide. The mixture is stirred at 30°-50° for about one hour, during which time a solution of 6.0 g (0.10 mole) of acetic acid in 20 ml of ethanol is slowly dripped in. After addition is complete, the mixture is cooled to room temperature and the solvent is removed under vacuum. The residue is partitioned between water and CH2Cl2, the layers separated, and the water extracted further with CH2Cl2. The combined organic layers are dried (Na2SO4) and the solvent is removed to give the crude product. This is purified by flash chromatography on silica gel to give ethyl 4-cyano-2-oxo-butanoate as an oil.

Workup

  1. additionAfter addition
  2. customthe solvent is removed under vacuum
  3. customThe residue is partitioned between water and CH2Cl2
  4. customthe layers separated
  5. extractionthe water extracted further with CH2Cl2
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. customthe solvent is removed
  8. customto give the crude product
  9. customThis is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-380bc57ebe424cee92c47c7d9d2a6d7e
Source dataset
uspto-grants-1998_06
Patent number
US05760021

Reaction notes

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