Trifluoroacetic acid → 3-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-hydroxybenzoic acid methyl ester

HRID 2355011Notes

Reaction equation

HRID 2355011 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:16]=[C:15]([O:17]COC)[CH:14]=[C:13]([O:21][C:22]2[CH:23]=[N:24][C:25]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[CH:26][CH:27]=2)[CH:12]=1>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:33])[C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([O:21][C:22]2[CH:23]=[N:24][C:25]([S:28]([CH2:31][CH3:32])(=[O:30])=[O:29])=[CH:26][CH:27]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687119443-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-methoxymethoxybenzoic acid methyl ester

Product 1

HCID 547540143-(6-Ethanesulfonyl-pyridin-3-yloxy)-5-hydroxybenzoic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 30.0 ml of trifluoroacetic acid to a solution of 11.8 g (30.9 mmol) of the obtained ester compound in methylene chloride (50.0 ml), the reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1) to obtain 8.86 g of 3-(6-ethanesulfonyl-pyridin-3-yloxy)-5-hydroxybenzoic acid methyl ester (yield: 85%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=2:1)

Sources & evidence

ORD record
ord-43fd07961517480dbbbbebb93deed326
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

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