2-Methoxy-4,6-dimethyl-3-vinylpyridine → 3-Ethyl-2-methoxy-4,6-dimethylpyridine

HRID 1921335Notes

Reaction equation

HRID 1921335 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]=[CH2:10])=[C:7]([CH3:11])[CH:6]=[C:5]([CH3:12])[N:4]=1>[Pd].C(O)C>[CH2:9]([C:8]1[C:3]([O:2][CH3:1])=[N:4][C:5]([CH3:12])=[CH:6][C:7]=1[CH3:11])[CH3:10]

Participants

4

Reactant 1

HCID 674925022-Methoxy-4,6-dimethyl-3-vinylpyridine

Product 1

HCID 674923843-Ethyl-2-methoxy-4,6-dimethylpyridineYield 39.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the above 2-methoxy-4,6-dimethyl-3-vinylpyridine (0.66 g, 4.05 mmol), 5% palladium on charcoal and ethyl alcohol (10 mL) is stirred under an atmosphere of hydrogen for 4 hr. The catalyst is removed by filtration through a pad of Hi-Flo and the filtrate is concentrated. The residue is purified by chromatography eluting with dichloromethane. Product containing fractions are combined and concentrated to afford 3-ethyl-2-methoxy-4,6-dimethylpyridine (265 mg, 22.4% yield for two steps). LC/MS: MS m/e=166 (M+H); RT 3.76 min; 1H NMR (CDCl3, δ ppm) 6.50 (1H, s), 3.90 (3H, s); 2.58 (2H, q), 2.38 (3H, s); 2.21 (3H, s), 1.07 (3H, t).

Workup

  1. customThe catalyst is removed by filtration through a pad of Hi-Flo
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography
  4. washeluting with dichloromethane
  5. additionProduct containing fractions
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c26d4a6d17b498c8fe2f38aa6ddbb98
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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