Tetrahydrofuran → 4-Chloro-6-ethyl-3-methyl-2-(2,4,5-trimethyl-phenoxy)-pyridine 1-oxide

HRID 1760705Notes

Reaction equation

HRID 1760705 reaction equation
C[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[C:19]([CH3:20])=[C:18]([Cl:21])[CH:17]=[C:16]([CH2:22][CH3:23])[N+:15]=1[O-:24].[CH2:25]1COCC1>>[Cl:21][C:18]1[CH:17]=[C:16]([CH2:22][CH3:23])[N+:15]([O-:24])=[C:14]([O:10][C:3]2[CH:2]=[C:7]([CH3:25])[C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])[C:19]=1[CH3:20]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 219123052,4-Dichloro-6-ethyl-3-methyl-pyridine 1-oxide

Product 1

HCID 225960254-Chloro-6-ethyl-3-methyl-2-(2,4,5-trimethyl-phenoxy)-pyridine 1-oxide

Procedure

To a solution of 2,4,6-trimethylphenol in dry THF was added NaH and stirred at room temperature for 20 minutes. A solution of 2,4-dichloro-6-ethyl-3-methyl-pyridine 1-oxide was added and the resulting mixture was heated at reflux for 1.5 hour. The mixture was cooled to room temperature, quenched with water, extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give the title compound which was used directly for the next step reaction.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1.5 hour
  3. temperatureThe mixture was cooled to room temperature
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-12291451298a4acf8462b426fe4417c7
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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