Ethyl Acetate → 2-Ethyl-6-methoxypyridine

HRID 2390794Notes

Reaction equation

HRID 2390794 reaction equation
C(C1C=C([C:15]2[C:16]([O:21][CH3:22])=[N:17][CH:18]=[CH:19][CH:20]=2)C=CC=1OC(F)F)(C)(C)C.[CH3:23][CH2:24]OC(C)=O>CCO.[Pd]>[CH2:23]([C:18]1[CH:19]=[CH:20][CH:15]=[C:16]([O:21][CH3:22])[N:17]=1)[CH3:24]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 670700073-(3-Tert-butyl-4-difluoromethoxy-phenyl)-2-methoxy-pyridine

Product 1

HCID 53247772-Ethyl-6-methoxypyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

step 2—A mixture of 22 (1.95 g) and Pd/C (10% wt. on carbon, 50 mg) in EtOAc (15 mL) and EtOH (15 mL) at RT was stirred under 1 atmosphere of H2 for 45 min. The catalyst was filtered off and the filtrate was concentrated. The crude residue was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 5% EtOAc) to afford 560 mg of 2-ethyl-6-methoxypyridine (26) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was purified by SiO2 chromatography
  4. washeluting with a EtOAc/hexane gradient (0 to 5% EtOAc)

Sources & evidence

ORD record
ord-f4997f4d0c034a02913eb5820e9d2182
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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