HCID 66933544, compound → HCID 66933548, compound

HRID 1908806Notes

Reaction equation

HRID 1908806 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH:13]=[C:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5])[CH3:2]>C1COCC1.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH2:13][CH:14]([CH3:15])[CH3:16])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 66933544HCID 66933544, compound

Product 1

HCID 66933548HCID 66933548, compoundYield 98.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-methyl-6-(2-methyl-propenyl)-pyridine-2-carboxylic acid ethyl ester (175 mg, 0.80 mmol) in THF (5 mL) and ethanol (5 mL), Pd/C (50 mg, 10% Pd) is added. The mixture is stirred at 50° C. for 15 h under 1 bar of H2. The catalyst is filtered off over celite and the solvent of the filtrate is evaporated to give 6-isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester (174 mg) as a colourless oil; LC-MS: tR=0.84 min, [M+1]+=222.48.

Workup

  1. filtrationThe catalyst is filtered off over celite
  2. customthe solvent of the filtrate is evaporated

Sources & evidence

ORD record
ord-7f5f563cae6b40f691b55e17508d431d
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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