Ethyl 3-oxohexanoate → ethyl (2E)-3-amino-2-hexenoate

HRID 478313Notes

Reaction equation

HRID 478313 reaction equation
[C:1]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])(=O)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[NH4+:16]>C(O)C>[NH2:16]/[C:1](/[CH2:2][CH2:3][CH3:4])=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 238498Ethyl 3-oxohexanoateHCID 517165Ammonium Acetate

Product 1

HCID 10986503ethyl (2E)-3-amino-2-hexenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl butyrylacetate (2.7 g, 17 mmol) in ethanol (7 mL) was treated with ammonium acetate (2.0, 26 mmol) and heated to reflux in a seated tube for 16 hours, cooled to ambient temperature and concentrated. The residue was purified by chromatography eluting with 2% methanol in ammonia saturated dichloromethane to provide the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux in a seated tube for 16 hours
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography
  5. washeluting with 2% methanol in ammonia saturated dichloromethane

Sources & evidence

ORD record
ord-774bc90967d44155a7f84fdd2414c7b0
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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