Tetrahydrofuran → 4-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one

HRID 15032Notes

Reaction equation

HRID 15032 reaction equation
C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][N:35]([C:38]2[CH:43]=[CH:42][C:41]([O:44][Si](C(C)(C)C)(C)C)=[CH:40][CH:39]=2)[C:34](=[O:52])[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)(=O)C>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][N:35]([C:38]2[CH:39]=[CH:40][C:41]([OH:44])=[CH:42][CH:43]=2)[C:34](=[O:52])[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 684303014-benzyloxy-1-{4-[tert-butyl(dimethyl)silyloxy]phenyl}-1H-pyridin-2-one

Product 1

HCID 684312834-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A THF solution (0.7 mL) of 1N tetrabutylammonium fluoride was added to a THF solution (2 mL) of 4-benzyloxy-1-{4-[tert-butyl(dimethyl)silyloxy]phenyl}-1H-pyridin-2-one (234 mg, 0.573 mmol) and stirred for 30 minutes at room temperature. Ethyl acetate was added to the reaction liquid, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the title compound (166 mg, 99%) was obtained.

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-c589eb62117e423e81d087932949699e
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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