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

HRID 2354017Notes

Reaction equation

HRID 2354017 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-e0cb1b6b64084e03ab1d4297a603fa4c
Source dataset
uspto-grants-2010_07
Patent number
US07750150B2

Reaction notes

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