Water → 1-(4-Methoxyphenyl)-2-(pyridin-4-yl)ethan-1-one

HRID 1062613Notes

Reaction equation

HRID 1062613 reaction equation
C(NC(C)C)(C)C.[N:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[C:15](OCC)(=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.O>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15](=[O:24])[CH2:14][C:11]2[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 79634-MethylpyridineHCID 60979Ethyl anisate

Product 1

HCID 100824531-(4-Methoxyphenyl)-2-(pyridin-4-yl)ethan-1-oneYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of diisopropylamine (33.2 mL) in anhydrous tetrahydrofuran (300 mL) was cooled to −78° C. and 1.6 M n-butyllithium-hexane solution (148 mL) was added dropwise with stirring. After completion of dropwise addition, the mixture was stirred for 10 min at the same temperature, then γ-picoline (20 g) was added dropwise. The temperature was raised to −10-0° C., and after stirring for 20 min, a solution of ethyl p-anisate (19.4 g) in anhydrous tetrahydrofuran (40 mL) was added dropwise. After completion of dropwise addition, the mixture was stirred at room temperature for 1 h, and water (100 mL) was added. The organic solvent was evaporated under reduced pressure and an oily product was extracted with ethyl acetate. The extract was washed with water, and after drying, the solvent was evaporated. the remaining crude crystals were recrystallized from ethyl acetate-isopropyl ether to give the title compound (16.2 g, yield 66%).

Workup

  1. addition1.6 M n-butyllithium-hexane solution (148 mL) was added dropwise
  2. additionAfter completion of dropwise addition
  3. stirringthe mixture was stirred for 10 min at the same temperature
  4. stirringafter stirring for 20 min
  5. additionAfter completion of dropwise addition
  6. stirringthe mixture was stirred at room temperature for 1 h
  7. customThe organic solvent was evaporated under reduced pressure
  8. extractionan oily product was extracted with ethyl acetate
  9. washThe extract was washed with water
  10. customafter drying
  11. customthe solvent was evaporated
  12. customthe remaining crude crystals were recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-2c3ae35b27d44c6abe7e2b4a4bcd148f
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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