Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one

HRID 15035Notes

Reaction equation

HRID 15035 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38]C3CCCCO3)=[CH:34][CH:33]=2)[C:28](=[O:45])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([C:32]2[CH:33]=[CH:34][C:35]([OH:38])=[CH:36][CH:37]=2)[C:28](=[O:45])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 684306714-benzyloxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one

Product 1

HCID 684312834-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridinium p-toluenesulfonate (65 mg) was added to an ethanol solution (16 mL) of 4-benzyloxy-1-{4-[(2-tetrahydropyranyl)oxy]phenyl}-1H-pyridin-2-one (982 mg, 2.60 mmols) and refluxed for an hour. The reaction liquid was cooled to room temperature and the precipitate was recovered by filtration and washed with water and ethyl acetate to provide the title compound (746 mg, 98%).

Workup

  1. temperaturerefluxed for an hour
  2. customThe reaction liquid
  3. filtrationthe precipitate was recovered by filtration
  4. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-7d8e8bb1d0ff40a88da8478839fb9b50
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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