Tetrahydrofuran → 4-Ethyl-2,3,5-trimethyl-1-oxo-1lambda~5~-pyridine

HRID 1693332Notes

Reaction equation

HRID 1693332 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=1[CH3:11].O1CC[CH2:14][CH2:13]1.C([Al](CC)CC)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[CH2:13]([C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-:9])=[C:4]([CH3:10])[C:3]=1[CH3:11])[CH3:14]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 16682930TriethylaluminumHCID 167371384-Bromo-2,3,5-trimethyl-1-oxo-1lambda~5~-pyridine

Product 1

HCID 672799884-Ethyl-2,3,5-trimethyl-1-oxo-1lambda~5~-pyridineYield 87%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

A mixture composed of 4-bromo-2,3,5-trimethylpyridine 1-oxide (5.76 g), tetrahydrofuran (60 mL), a 15% solution of triethylaluminum in toluene (40 mL) and tetrakis(triphenylphosphine)palladium (0) (1.54 g) was heated under reflux for six hours. After leaving to cool to room temperature, toluene (60 mL), methanol (12 mL) and subsequently a saturated ammonium chloride solution (18 mL) were added, and the mixture was heated under reflux for one hour. After leaving to cool to room temperature, the insoluble matter was separated off by filtration, and the filtrate was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (3.84 g, 87%) as an oil.

Workup

  1. temperatureunder reflux for six hours
  2. customAfter leaving
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for one hour
  5. customAfter leaving
  6. temperatureto cool to room temperature
  7. customthe insoluble matter was separated off by filtration
  8. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-889a0a134cd1469890a714d0d8f19c83
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

Loading…