Ethyl 4,4,4-trifluoroacetoacetate → HCID 178472917, compound

HRID 1492495Notes

Reaction equation

HRID 1492495 reaction equation
[N:1]([O-:3])=O.[Na+].[F:5][C:6]([F:16])([F:15])[C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>O.C(O)(=O)C>[F:5][C:6]([F:15])([F:16])[C:7](=[O:14])[C:8](=[N:1][OH:3])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472917HCID 178472917, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

A solution of sodium nitrite (0.29 mmol) in 35 mL of water was added dropwise over 50 minutes to a stirred, ice-cooled solution of 22.8 g of ethyl 4,4,4-trifluoroacetoacetate (0.12 mmol) in 30 mL of acetic acid. The reaction was continued for 2 hours, with gradual warming to 15° C. Water and acetic acid were removed under reduced pressure (azeotroped with toluene). The crude product was partitioned between ethyl acetate and saturated aqueous potassium hydrogen carbonate solution. The layers were separated. The ethyl acetate layer was washed with saturated aqueous potassium hydrogen carbonate solution and brine, dried over sodium sulfate and concentrated to yield 21.4 g of the title A compound as a light yellow oil.

Workup

  1. customWater and acetic acid were removed under reduced pressure (azeotroped with toluene)
  2. customThe crude product was partitioned between ethyl acetate and saturated aqueous potassium hydrogen carbonate solution
  3. customThe layers were separated
  4. washThe ethyl acetate layer was washed with saturated aqueous potassium hydrogen carbonate solution and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a853ad9a1e5d49d9b9ca800d8fdc2d4b
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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