Hydrochloric Acid → 2-Chloro-6-(trifluoroacetoacetyl)pyridine

HRID 1859394Notes

Reaction equation

HRID 1859394 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:21])[CH3:20])[N:14]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.Cl>C1COCC1.C(O)C>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19](=[O:21])[CH2:20][C:3]([C:2]([F:1])([F:8])[F:9])=[O:5])[N:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydrideHCID 26541Dibenzo-18-crown-6HCID 115791671-(6-Chloropyridin-2-yl)ethanone

Product 1

HCID 116012682-Chloro-6-(trifluoroacetoacetyl)pyridine

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a mixture of ethyl trifluoroacetate (17.2 g) and sodium hydride (60% in oil, 5.7 g) in THF (200 ml) is added a solution of 1A (11.2 g) in THF (50 ml) with ethanol (2 drops) and a solution of dibenzo-18-crown-6 (415 mg) in THF (70 ml). The reaction mixture is stirred for 60 h at ambient temperature. After heating for 1 h at reflux temperature, the mixture is acidified with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase is dried and evaporated. One obtains the crude title compound as an oily product (21.5 g).

Workup

  1. temperatureAfter heating for 1 h
  2. temperatureat reflux temperature
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated

Sources & evidence

ORD record
ord-d3c2dbb0fcf7488bbcacf0dcf21a7e67
Source dataset
uspto-grants-2003_03
Patent number
US06528456B2

Reaction notes

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