2,6-Divinyl-isonicotinic acid tert-butyl ester → 2,6-Diethylisonicotinic acid tert-butyl ester

HRID 1908729Notes

Reaction equation

HRID 1908729 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH:13]=[CH2:14])[N:10]=[C:9]([CH:15]=[CH2:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=[C:9]([CH2:15][CH3:16])[CH:8]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 670270962,6-Divinyl-isonicotinic acid tert-butyl ester

Product 1

HCID 670269262,6-Diethylisonicotinic acid tert-butyl esterYield 88.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2,6-divinyl-isonicotinic acid tert-butyl ester (703 mg, 3.04 mmol) in methanol (15 mL), Pd/C (50 mg, 10% Pd) is added and the mixture is stirred under 1 atm of H2 at rt for 15 h. The catalyst is filtered off and the filtrate is evaporated. The remaining residue is purified by CC on silica gel eluting with heptane:EA 5:1 to give 2,6-diethyl-isonicotinic acid tert-butyl ester (635 mg) as a colourless oil; LC-MS: tR=1.05 min, [M+1]+=236.13.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe remaining residue is purified by CC on silica gel eluting with heptane:EA 5:1

Sources & evidence

ORD record
ord-c031282fff3e4c7989578d03c02ec71d
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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