Ethyl 5-(prop-1-en-2-yl)pyridine-2-carboxylate → Ethyl 5-(propan-2-yl)pyridine-2-carboxylate

HRID 70510Notes

Reaction equation

HRID 70510 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8][CH:9]=1)[CH3:3].[H][H]>C(O)C.[Pd]>[CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8][CH:9]=1)([CH3:3])[CH3:1]

Participants

5

Reactant 2

HCID 57662632Ethyl 5-(prop-1-en-2-yl)pyridine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 13624110Ethyl 5-(propan-2-yl)pyridine-2-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium-activated carbon (5.8 g) was added to a solution of ethyl 5-(prop-1-en-2-yl)pyridine-2-carboxylate (10 g) in ethanol (100 mL), and the mixture was stirred in a hydrogen gas stream at room temperature overnight. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→0:1) to give ethyl 5-isopropylpyridine-2-carboxylate as a colorless oil (10 g, 95%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→0:1)

Sources & evidence

ORD record
ord-6557191e294c4fcabd50a3d1b0ae2c22
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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