Water → 2-(5-Methylpyridin-3-yl)-1-phenylethan-1-one

HRID 1062614Notes

Reaction equation

HRID 1062614 reaction equation
C(NC(C)C)(C)C.[N:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1.[C:16](OCC)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>O1CCCC1>[CH3:14][C:12]1[CH:11]=[C:10]([CH2:15][C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:23])[CH:9]=[N:8][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7165Ethyl benzoateHCID 7912DiisopropylamineHCID 115653,5-Dimethylpyridine

Product 1

HCID 125824092-(5-Methylpyridin-3-yl)-1-phenylethan-1-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of diisopropylamine (20.2 mL) in anhydrous tetrahydrofuran (180 mL) was cooled to −78° C., and a 1.6 M n-butyllithium-hexane solution (90 mL) was added dropwise with stirring. After completion of dropwise addition, the mixture was stirred for 10 min at the same temperature, and then 3,5-lutidine (14 g) was added dropwise. The temperature was raised to −10-0° C., and after stirring for 20 min, a solution of ethyl benzoate (9.8 g) in anhydrous tetrahydrofuran (20 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 (10 g, yield 70%).

Workup

  1. additiona 1.6 M n-butyllithium-hexane solution (90 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-e6c8d015bedf437e81274d9c600a1c37
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

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