Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate → Ethyl 3-(6-methyl-3-pyridyl)propionate

HRID 53199Notes

Reaction equation

HRID 53199 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54365744Ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate

Product 1

HCID 3018102Ethyl 3-(6-methyl-3-pyridyl)propionateYield 96.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of ethyl β-(6-methylpyridin-3-yl)acrylate (3.86 g, 20.2 mmol) in 200 ml of ethyl acetate and 1.4 g of 5.3% Pd/C was hydrogenated under hydrogen (50 psi) for 4 h. The mixture was filtered through SUPERCEL™, the filtrate was concentrated in vacuo to afford 3.75 g (96%) of ethyl 3-(6-methylpyridin-3-yl)propionate, as a pale orange oil.

Workup

  1. filtrationThe mixture was filtered through SUPERCEL™
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-62151cd0315d4989aa6b9360c861e1f5
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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