Ethanol → HCID 68769001, compound

HRID 2065889Notes

Reaction equation

HRID 2065889 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([CH:11]=[CH2:12])[C:8]([CH:13]=[C:14]([CH3:16])[CH3:15])=[N:7][CH:6]=1)[CH3:2].CCO>C1COCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([CH2:11][CH3:12])[C:8]([CH2:13][CH:14]([CH3:15])[CH3:16])=[N:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 68762683HCID 68762683, compound

Product 1

HCID 68769001HCID 68769001, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To solution of 6-(2-methyl-propenyl)-5-vinyl-nicotinic acid ethyl ester (1.37 g, 6.74 mmol) in THF (20 mL), Pd/C (100 mg, 10% Pd) followed by EtOH (20 mL) is added. The mixture is stirred under 1 atm of H2 at rt for 24 h. The catalyst is removed by filtration and the filtrate is concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 5-ethyl-6-isobutyl-nicotinic acid ethyl ester (970 mg) as a colourless oil, LC-MS: tR=0.79 min, [M+1]+=236.20; 1H NMR (CDCl3): δ0.97 (d, J=6.8 Hz, 6H), 1.27 (t, J=7.5 Hz, 3H), 1.42 (t, J=7.0 Hz, 3H), 2.17-2.28 (m, 1H), 2.69-2.78 (m, 4H), 4.42 (q, J=7.0 Hz, 2H), 8.07 (s, 1H), 9.00 (s, 1H).

Workup

  1. additionis added
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated
  4. customThe crude product is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-7c0c25206e084f8aa7b22c97c0777dfb
Source dataset
uspto-grants-2012_10
Patent number
US08288554B2

Reaction notes

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