Methyl iodide → 1-(2-Methyl-pyridin-4-yl)-2-phenyl-propan-1-one

HRID 333762Notes

Reaction equation

HRID 333762 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:19]I>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:16])[CH:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:19])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574213301-(2-Methyl-pyridin-4-yl)-2-phenyl-ethanone

Product 1

HCID 574213311-(2-Methyl-pyridin-4-yl)-2-phenyl-propan-1-oneYield 57.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Methyl-pyridin-4-yl)-2-phenyl-ethanone (233 mg, 1.1 mmol, solution in 5 mL DMF) was added over 15 min to a suspension of NaH (55% in mineral oil, 58 mg, 1.3 mmol) in DMF (2 mL). After 30 min, methyl iodide (0.07 mL, 1.2 mmol) was added slowly drop by drop. The mixture was poured onto ice and extracted with ethyl acetate. The combined organic layers were washed (brine), dried (Na2SO4), and the solvent was evaporated. Purification by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50) afforded the title compound (142 mg, 54%). 1H NMR (300 MHz, DMSO-D6) 8.56 (1H, d), 7.68 (1H, s), 7.61 (1H, d), 7.30-7.27 (4H, m), 7.20-7.18 (1H, m), 4.92 (1H, q), 1.40 (3H, d); MS (m/e)=226.3 [MH+].

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed (brine)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated
  6. customPurification by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50)

Sources & evidence

ORD record
ord-d3e5e704b2a74972b33e1e1d9207185b
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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