3-(6-Methylpyridin-2-yl)acrylic acid ethyl ester → Ethyl 3-(6-methylpyridin-2-yl)propanoate

HRID 1788387Notes

Reaction equation

HRID 1788387 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)[CH3:2]>CO.[C].[Pd]>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 673561473-(6-Methylpyridin-2-yl)acrylic acid ethyl ester

Product 1

HCID 57602865Ethyl 3-(6-methylpyridin-2-yl)propanoateYield 77.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.39 g (7.85 mmol) of 3-(6-methylpyridin-2-yl)acrylic acid ethyl ester in methanol (50 mL) was added 200 mg of 10% palladium-carbon, and stirred for 4 hours at room temperature under an atmosphere of hydrogen. The solution was filtered through Celite and the obtained filtrate was concentrated under a reduced pressure. The residue was purified by silica gel chromatography (developing solvent; hexane:ethyl acetate=3:1 to 2:1) to obtain 1.09 g (6.09 mmol) of 3-(6-methylpyridin-2-yl)propionic acid ethyl ester (IX-129) as colorless oil. Its physical property is shown below.

Workup

  1. filtrationThe solution was filtered through Celite
  2. concentrationthe obtained filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by silica gel chromatography (developing solvent; hexane:ethyl acetate=3:1 to 2:1)

Sources & evidence

ORD record
ord-ef36f3dab449480895fef773192a1f2a
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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