3-Benzyloxy-5-(Trifluoromethyl)Pyridine → 5-(Trifluoromethyl)pyridin-3-ol

HRID 2171354Notes

Reaction equation

HRID 2171354 reaction equation
C([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[F:18][C:15]([F:16])([F:17])[C:13]1[CH:14]=[C:9]([OH:8])[CH:10]=[N:11][CH:12]=1

Participants

4

Reactant 1

HCID 218518253-Benzyloxy-5-(Trifluoromethyl)Pyridine

Product 1

HCID 229897075-(Trifluoromethyl)pyridin-3-olYield 38.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(benzyloxy)-5-(trifluoromethyl)pyridine (10 g, 39.5 mmol) in methanol (100 mL) was added Pd/C (0.500 g, 4.70 mmol). The reaction mixture was stirred at 50° C. under H2 (55 psi) for 24 h, filtered and concentrated under reduce pressure to afford the crude product (2.5 g).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5bc1abbe719149f9a067e0bc49e33ad9
Source dataset
uspto-grants-2015_06
Patent number
US09051325B2

Reaction notes

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