Sodium Bicarbonate → Ethyl 2,4-difluoro-3-amino-2-butenoate

HRID 1649555Notes

Reaction equation

HRID 1649555 reaction equation
[F:1][CH:2]([C:8](=O)[CH2:9][F:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])(=O)C.[NH4+:16].C(=O)(O)[O-].[Na+]>CO>[F:1][C:2](=[C:8]([NH2:16])[CH2:9][F:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 15207128Ethyl 2,4-difluoro-3-oxobutanoate

Product 1

HCID 86020216Ethyl 2,4-difluoro-3-amino-2-butenoateYield 45.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 2,4-difluoro-3-oxobutanoate (24.6 g, 0.148 mol), ammonium acetate (200 g, 2.6 mol) and anhydrous methanol (400 mL) is stirred at room temperature for 3 days. The solution is poured into a saturated aqueous solution of sodium bicarbonate (1L) and extracted four times with ether. The combined organic phases are washed with brine and dried over magnesium sulfate. The solvent is evaporated to yield ethyl 2,4-difluoro-3-amino-2-butenoate (11.1 g, 45%)

Workup

  1. extractionextracted four times with ether
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent is evaporated

Sources & evidence

ORD record
ord-1431f428058743c0a055444f4d89764d
Source dataset
uspto-grants-1983_11
Patent number
US04418077

Reaction notes

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