Water → Ethyl 4,4-difluoroacetoacetate

HRID 1667542Notes

Reaction equation

HRID 1667542 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[O-:7]CC.[Na+].[F:11][C:12](N(C)C)([F:16])[CH:13](F)F.O>C(O)C>[F:11][CH:12]([F:16])[C:13](=[O:7])[CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2723922Sodium ethoxideHCID 21945697Ethanamine, 1,1,2,2-tetrafluoro-N,N-dimethyl-

Product 1

HCID 67697Ethyl 4,4-difluoroacetoacetateYield 65.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An initial charge of 48 g of ethyl acetate was admixed at RT with a 10% solution of 32.4 g of sodium ethoxide in ethanol. The mixture was stirred at RT for 1 h and then admixed with 36 g of 1,1,2,2-tetrafluoroethyldimethylamine. Subsequently, the solution was stirred at 30° C. for 2 h, admixed with H2O and adjusted to pH 5. After extraction with ethyl acetate and subsequent distillation, 27 g (65%) of ethyl difluoroacetoacetate (boiling point 90-94° C./100 mbar) were obtained.

Workup

  1. stirringSubsequently, the solution was stirred at 30° C. for 2 h
  2. extractionAfter extraction
  3. distillationwith ethyl acetate and subsequent distillation

Sources & evidence

ORD record
ord-2c4a44d24b614e3ea480352504f6c09c
Source dataset
uspto-grants-2011_10
Patent number
US08044231B2

Reaction notes

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