Methanol → HCID 67027121, compound

HRID 1908767Notes

Reaction equation

HRID 1908767 reaction equation
[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH:13]=[CH2:14])[C:10]([CH:15]=[CH2:16])=[N:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:17])[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([CH2:15][CH3:16])=[N:9][CH:8]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 67026987HCID 67026987, compound

Product 1

HCID 67027121HCID 67027121, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-divinyl-nicotinic acid tert-butyl ester (890 mg, 3.8 mmol) in THF (20 mL) containing some methanol, Pd/C (100 mg, 10% Pd) is added and the mixture is stirred under 1 atm of H2 at rt for 3 h. The catalyst is filtered off and the filtrate is evaporated. The remaining residue is purified by FC (SiO2, EA-heptane) to give 5,6-diethyl-nicotinic acid tert-butyl ester (860 mg) as an oil; LC-MS: tR=0.79 min, [M+1]+=236.14.

Workup

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customThe remaining residue is purified by FC (SiO2, EA-heptane)

Sources & evidence

ORD record
ord-889a8acac4024f0988e88ea7985ac46a
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

Loading…