Acetone → Ethyl 4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylate

HRID 1251952Notes

Reaction equation

HRID 1251952 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].C([O-])([O-])=O.[K+].[K+].[CH2:24](I)[CH3:25].[CH3:27][C:28](C)=O>>[CH2:27]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:24][CH3:25])[N:5]=[C:4]([C:9]([F:12])([F:10])[F:11])[C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH3:28]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178470040HCID 178470040, compound

Product 1

HCID 13726789Ethyl 4,6-diethoxy-2-(trifluoromethyl)-3-pyridinecarboxylateYield 82.9%

Procedure

This material was prepared in 82.9% yield from product of Example 1 (1 eq), K2CO3 (2 eq) and excess ethyl iodide. The reaction mixture was refluxed in acetone for 18 hours and filtered. The filtrate was concentrated. The residue was dissolved in ether. The ether solution was washed with 10% K2CO3, dried (MgSO4) and concentrated to give the product as an oil, nD25 1.4534.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ether
  4. washThe ether solution was washed with 10% K2CO3
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-efe1bed73b714a7e80930fbb3e47aa1b
Source dataset
uspto-grants-1988_05
Patent number
US04741766

Reaction notes

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