Acetoacetamide → HCID 86688228, compound

HRID 868890Notes

Reaction equation

HRID 868890 reaction equation
C(O[CH:4]=[CH:5][C:6](=O)[C:7]([F:10])([F:9])[F:8])C.[C:12]([NH2:18])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].[O-]CC.[Na+:22]>C(O)C>[C:14]([C:13]1[C:12]([O-:17])=[N:18][C:6]([C:7]([F:8])([F:9])[F:10])=[CH:5][CH:4]=1)(=[O:15])[CH3:16].[Na+:22]

Participants

5

Reactant 3

HCID 80077AcetoacetamideHCID 2723922Sodium ethoxideHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Product 1

HCID 86688228HCID 86688228, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (4.21 g, 22.5 mmol), ethanol (42 mL), acetoacetamide (2.28 g, 22.5 mmol), and sodium ethoxide (21 wt % in ethanol, 8.41 mL, 22.5 mmol) was heated to 75° C. After 12 hours, the mixture was cooled to room temperature over 30 minutes, stirred for 4 hours, then cooled to <5° C. After 10 minutes, the white slurry was filtered, washing with cold ethanol (5 mL). The white solid was dried in a vacuum oven at 60° C. to provide the title compound (4.39 g, 19.3 mmol, 86% yield). MS (DCI) m/z 206 (M+H)+.

Workup

  1. temperaturecooled to <5° C
  2. waitAfter 10 minutes
  3. filtrationthe white slurry was filtered
  4. washwashing with cold ethanol (5 mL)
  5. customThe white solid was dried in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-d02c4c2b5d9c418b9441127cacbfb530
Source dataset
uspto-grants-2015_03
Patent number
US08969325B2

Reaction notes

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