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

HRID 2040773Notes

Reaction equation

HRID 2040773 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 MeOH (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-0bfb035091aa462c93d5c4b5fc15f0f3
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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