Ethyl 4,4,4-trifluoroacetoacetate → Ethyl 3-amino-4,4,4-trifluorocrotonate

HRID 1956002Notes

Reaction equation

HRID 1956002 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C([O-])(=O)C.[NH4+:17]>>[NH2:17]/[C:3](/[C:2]([F:12])([F:11])[F:1])=[CH:4]\[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetate2×HCID 517165Ammonium Acetate

Product 1

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonate

Conditions

Temperature
85 °C

Procedure

To a stirred ethyl trifluoroacetoacetate (87.8 g, 0.48 mol) at 85° C., ammonium acetate (74 0 g, 0.96 mol) was added in portions over 1 hour such that efficient stirring of the mixture was maintained. The mixture was heated at 85° C. for an additional 4 hours. After this period, GC analysis of the reaction mixture showed that the all the ethyl trifluoroacetoacetate had been consumed and the yield of ethyl 3-amino-4,4,4-trifluorocrotonate was greater than 98%.

Workup

  1. temperaturewas maintained
  2. waitAfter this period
  3. customhad been consumed

Sources & evidence

ORD record
ord-fb3585153e6e4659852438aa0362ad61
Source dataset
uspto-grants-1998_07
Patent number
US05777154

Reaction notes

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