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

HRID 706533Notes

Reaction equation

HRID 706533 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 93.2%

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 three times and then with hydrogen three times. A hydrogen balloon was applied to the reaction for three hours. The reaction was then purged with N2, filtered through Celite and washed with EtOH (100 mL). Solvent was removed under reduced pressure to give 4.36 g (93%) of ethyl 6-isopropylpicolinate.

Workup

  1. customThe reaction mixture was purged with nitrogen three times
  2. customA hydrogen balloon was applied to the reaction for three hours
  3. customThe reaction was then purged with N2
  4. filtrationfiltered through Celite
  5. washwashed with EtOH (100 mL)
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-885d3dc645b0449cbbfffc6d85500b27
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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