Citric Acid → 4,4,4-Trifluoro-1-(pyridin-4-yl)butane-1,3-dione

HRID 1710479Notes

Reaction equation

HRID 1710479 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].CO.[C:15]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)(=[O:17])[CH3:16].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>COC(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:16][C:15]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[O:17]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 9794Ethyl trifluoroacetateHCID 142824-AcetylpyridineHCID 23694274Sodium methanolate methanol

Product 1

HCID 2382984,4,4-Trifluoro-1-(pyridin-4-yl)butane-1,3-dioneYield 62.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Ethyl trifluoroacetate (6.32 g) was dissolved in tert-butyl methyl ether (10 mL) and a 28% sodium methoxide-methanol solution (9.40 g) and a solution of 4-acetylpyridine (4.90 g) in tert-butyl methyl ether (20 mL) were added successively at room temperature. The mixture was stirred for 22 hr. A 10% a aqueous citric acid solution was added until the reaction solution became about pH 4, and the precipitate was collected by filtration, washed with water and dried to give 4-trifluoroacetoacetylpyridine (5.46 g) as a yellow solid.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c1e2cbb8b1d34eb6bd2f533a81fd576a
Source dataset
uspto-grants-2010_09
Patent number
US07790725B2

Reaction notes

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