Furfural → HCID 12600432, compound

HRID 847448Notes

Reaction equation

HRID 847448 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[F:8][C:9]([F:19])([F:18])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH-:20].[NH4+:21]>C(O)C>[F:8][C:9]([F:18])([F:19])[C:10]1([OH:17])[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:20])[C:10]([C:9]([F:8])([F:18])[F:19])([OH:17])[NH:21]1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 14923Ammonium HydroxideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 12600432HCID 12600432, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 mL 3 necked flask is charged with 60 mL ethanol, 29.07 g (0.3 mole) of 2-furaldehyde and 110 g (0.6 mole) of ethyl trifluoroacetoacetate. The reaction mixture is cooled in an ice bath before 21.15 21.15 g (0.35 mole) of aqueous ammonium hydroxide is added slowly with stirring. The mixture is heated at reflux for 2 hours and cooled. The resulting precipitate is filtered and recrystallized from hot ethanol to give 53.34 g (39%) of crystals, m.p 129°-131° C.

Workup

  1. additionis added slowly
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. filtrationThe resulting precipitate is filtered
  6. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-40ffba9a3ea946e1bdaa8fab1a24a790
Source dataset
uspto-grants-1992_08
Patent number
US05142055

Reaction notes

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