1,1,1-Trifluoro-2,4-pentanedione → Methyl 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylate

HRID 2373677Notes

Reaction equation

HRID 2373677 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3](=O)[CH2:4][C:5](=O)[CH3:6].[NH2:11]/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15]>C(#N)C>[CH3:18][C:12]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:3]([C:2]([F:10])([F:9])[F:1])[CH:4]=[C:5]([CH3:6])[N:11]=1

Participants

4

Reactant 2

HCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 23092426Methyl 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,1,1-Trifluoro-2,4-pentanedione (25.01 g, 135.3 mmol) was dissolved in acetonitrile (230 mL). Methyl 3-aminocrotonate (15.57 g, 135.2 mmol) was added to the solution, followed by refluxing for 20 hours. The reaction mixture was allowed to stand for cooling, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (eluent: n-hexane/acetone=10/1), to thereby yield methyl 2,6-dimethyl-4-trifluoromethylpyridine-3-carboxylate as a yellow oil (22.30 g, 71%).

Workup

  1. temperatureby refluxing for 20 hours
  2. temperaturefor cooling
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (eluent: n-hexane/acetone=10/1)

Sources & evidence

ORD record
ord-61283c8573184bcba55b2afe3b03eb07
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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