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

HRID 1896057Notes

Reaction equation

HRID 1896057 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-carboxylateYield 71%

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), followed by the addition of methyl 3-aminocrotonate (15.57 g, 135.2 mmol). The mixture was subjected to heating under reflux for 20 hours. The reaction mixture was allowed to cool down to room temperature, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (silica gel: 400 g; developer: hexane:acetone=10:1) to obtain the title compound (22.30 g, 71%) as a yellow oil.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 20 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (silica gel: 400 g; developer: hexane:acetone=10:1)

Sources & evidence

ORD record
ord-3fcffb1e4ec9471593bc4e72d8d685e4
Source dataset
uspto-grants-2013_08
Patent number
US08518936B2

Reaction notes

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