Tetrahydrofuran → 4-hydroxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one

HRID 15042

Reaction equation

HRID 15042 reaction equation
C1COCC1.C([O:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[CH:22][CH:21]=2)[C:16](=[O:33])[CH:15]=1)C1C=CC=CC=1>[Pd].CO>[OH:13][C:14]1[CH:19]=[CH:18][N:17]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)=[CH:24][CH:25]=2)[C:16](=[O:33])[CH:15]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 684306714-benzyloxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one

Product 1

HCID 684287684-hydroxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Into a THF (25 mL)-MeOH (25 mL) mixed solvent solution of 4-benzyloxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one (Step (1) of Example 12, 2.05 g, 5.4 mmols), 10% palladium-on-carbon (600 mg) was added. The atmosphere was hydrogen-substituted, and the reaction system was stirred at room temperature for 3.5 hours. The reaction liquid was filtered, the solvent was concentrated under reduced pressure, methanol was added to the resulting residue and the precipitate was recovered by filtration. Drying the same, the title compound (1.25 g, 80%) was obtained.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. concentrationthe solvent was concentrated under reduced pressure, methanol
  5. additionwas added to the resulting residue
  6. filtrationthe precipitate was recovered by filtration
  7. dry with materialDrying the same, the title compound (1.25 g, 80%)
  8. customwas obtained

Sources & evidence

ORD record
ord-4ed2fb8c276347ad8b5d9f43e33d617f
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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