Ethyl 4-chloroacetoacetate → HCID 12366516, compound

HRID 353469Notes

Reaction equation

HRID 353469 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O-])(=O)C.[NH4+:15]>C(O)C>[NH2:15]/[C:3](/[CH2:2][Cl:1])=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 517165Ammonium Acetate

Product 1

HCID 12366516HCID 12366516, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-chloroacetoacetate (7.02 ml) and ammonium acetate (11.8 g) in absolute ethanol (180 ml) is refluxed for 3 hours. After a night at room temperature the solution is concentrated to dryness by distillation under reduced pressure and the resulting residue is purified by flash chromatography (silica gel, 200 g; eluent CH2Cl2/MeOH/TEA 15/5/02), to give 6.53 g of ethyl (Z)-3-amino-4-chloro-2-butenoate as dark oil which is used without further purifications.

Workup

  1. concentrationAfter a night at room temperature the solution is concentrated to dryness by distillation under reduced pressure
  2. customthe resulting residue is purified by flash chromatography (silica gel, 200 g; eluent CH2Cl2/MeOH/TEA 15/5/02)

Sources & evidence

ORD record
ord-24866de84850439da6e781961c2fdce3
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

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