2-[2-(Benzyloxy)-4-ethylphenoxy]-6-fluoropyridine → 5-Ethyl-2-[(6-fluoropyridin-2-yl)oxy]phenol

HRID 625987Notes

Reaction equation

HRID 625987 reaction equation
C([O:8][C:9]1[CH:22]=[C:21]([CH2:23][CH3:24])[CH:20]=[CH:19][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:23]([C:21]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=2)=[C:9]([OH:8])[CH:22]=1)[CH3:24]

Participants

4

Reactant 1

HCID 591913542-[2-(Benzyloxy)-4-ethylphenoxy]-6-fluoropyridine

Product 1

HCID 167527195-Ethyl-2-[(6-fluoropyridin-2-yl)oxy]phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[2-(benzyloxy)-4-ethylphenoxy]-6-fluoropyridine (28 mg; 0.09 mmol) was dissolved in ethanol (4 mL), under argon. Palladium on charcoal (4 mg; 0.02 mmol) was added and the reaction was flushed twice with hydrogen, then left to stir overnight at room temperature. The reaction mixture was filtered on celite, then rinsed with methanol (3*3 mL). Concentration yielded a white solid (25 mg; 98%) of title compound.

Workup

  1. customthe reaction was flushed twice with hydrogen
  2. waitleft
  3. filtrationThe reaction mixture was filtered on celite
  4. washrinsed with methanol (3*3 mL)
  5. concentrationConcentration

Sources & evidence

ORD record
ord-d3f6ba1de4fc4a25a90485aacd9edd5d
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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