Ethyl 6-(prop-1-en-2-yl)picolinate → Ethyl 6-isopropylpicolinate

HRID 706723Notes

Reaction equation

HRID 706723 reaction equation
[CH2:1]=[C:2]([C:4]1[N:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=1)[CH3:3]>CCO.[Pd]>[CH:2]([C:4]1[N:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 67974687Ethyl 6-(prop-1-en-2-yl)picolinate

Product 1

HCID 67974663Ethyl 6-isopropylpicolinateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To ethyl 6-(prop-1-en-2-yl)picolinate (4.63 g, 24.2 mmol) in EtOH (50 mL) was added Pd/C (0.61 g, 0.573 mmol). The reaction mixture was purged with nitrogen and hydrogen three times each. A hydrogen balloon was applied to the reaction for three hours. The reaction was then purged with nitrogen, filtered through Celite® and washed with EtOH (100 mL). Solvent was removed under reduced pressure to give the desired product (93%).

Workup

  1. customThe reaction mixture was purged with nitrogen and hydrogen three times each
  2. customA hydrogen balloon was applied to the reaction for three hours
  3. customThe reaction was then purged with nitrogen
  4. filtrationfiltered through Celite®
  5. washwashed with EtOH (100 mL)
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a60ecab01f16470b85fe20fcb765939a
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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