Methyl 3-(4-methoxypyridin-2-yl)acrylate → Methyl 3-(4-methoxypyridin-2-yl)propanoate

HRID 133101Notes

Reaction equation

HRID 133101 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])[CH:4]=1>CO.[Pd]>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 1

HCID 68407789Methyl 3-(4-methoxypyridin-2-yl)acrylate2×

Product 1

HCID 21882722Methyl 3-(4-methoxypyridin-2-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

43.1 g of methyl 3-(4-methoxypyridin-2-yl)acrylate (starting material F3) in 600 ml of methanol are hydrogenated over 3.0 g of Pd/C (10%) until the starling material has disappeared (TLC). The catalyst is filtered off, and the mixture is then concentrated and dried under high vacuum. This gives 41.95 g of the title compound as a light-yellow oil. The mass spectrum shows the molecular peak MH+ at 196 Da.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe mixture is then concentrated
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-f8fd19aaf7734f66bab7e37a377e38a2
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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