Trifluoroacetic acid → 4-[(E)-2-(4-hydroxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)-ethoxy]phenyl}-1H-pyridin-2-one

HRID 15054Notes

Reaction equation

HRID 15054 reaction equation
FC(F)(F)C(O)=O.CC([O:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:29][CH:28]=3)[C:23](=[O:41])[CH:22]=2)=[CH:15][CH:14]=1)(C)C>>[OH:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][N:24]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][CH2:39][CH2:40]4)=[CH:29][CH:28]=3)[C:23](=[O:41])[CH:22]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 684300224-((E)-2-{4-[(2-methyl-2-propyl)oxy]phenyl}vinyl)-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one

Product 1

HCID 684306454-[(E)-2-(4-hydroxyphenyl)vinyl]-1-{4-[2-(1-pyrrolidinyl)-ethoxy]phenyl}-1H-pyridin-2-oneYield 92.7%

Procedure

Trifluoroacetic acid (2 mL) was added to 4-((E)-2-{4-[(2-methyl-2-propyl)oxy]phenyl}vinyl)-1-{4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-1H-pyridin-2-one (120 mg, 0.26 mmol) and stirred at room temperature for 30 minutes. After concentrating the reaction liquid under reduced pressure, chloroform was added to the reaction liquid which then was washed with aqueous sodium hydrogencarbonate solution and dried over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the title compound (97 mg, 92%) was obtained as a white solid.

Workup

  1. concentrationAfter concentrating
  2. customthe reaction liquid under reduced pressure, chloroform
  3. additionwas added to the reaction liquid which
  4. washthen was washed with aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-241179f0589349129fa9c34052951db9
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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