Benzyl Bromide → 1-(2,6-Dimethyl-pyridin-4-yl)-2-phenyl-ethanone

HRID 1617470Notes

Reaction equation

HRID 1617470 reaction equation
CON(C)[C:4](=[O:13])[C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([CH3:12])[CH:6]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Li]CCCC.[NH4+].[Cl-]>C1COCC1>[CH3:11][C:9]1[CH:10]=[C:5]([C:4](=[O:13])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[C:7]([CH3:12])[N:8]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 18736278N-Methoxy-N,2,6-trimethylisonicotinamideHCID 178418339Butyllithium

Product 1

HCID 666663811-(2,6-Dimethyl-pyridin-4-yl)-2-phenyl-ethanoneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., to a solution of N-methoxy-2,6,N-trimethyl-isonicotinamide (1 g) and benzyl bromide (0.73 mL) in THF (30 mL) was added n-BuLi (1.6M in hexane, 6.6 mL) dropwise. The reaction was stirred at −78° C. for 3 hours. A saturated aqueous solution of NH4Cl (200 mL) was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. Column chromatography on silica gel (EtOAc/n-heptane 1:2) yielded the title compound (1.8 g, 99%) as a colorless liquid, MS (ESI+): m/z=226.1 [M+H]+.

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4395006a59434204bc000bd0f3c3dd3b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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