Trifluoroacetic acid methylene chloride → 4-Methoxy-3-methyl-5-(2,2,2-trifluoro-acetoxymethyl)-benzofuran-2-carboxylic acid

HRID 29430Notes

Reaction equation

HRID 29430 reaction equation
C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH2:18][OH:19])=[C:14]([O:20][CH3:21])[C:11]=2[C:12]=1[CH3:13])=[O:7])(C)(C)C.[C:22](O)([C:24]([F:27])([F:26])[F:25])=[O:23].ClCCl>>[CH3:21][O:20][C:14]1[C:11]2[C:12]([CH3:13])=[C:8]([C:6]([OH:5])=[O:7])[O:9][C:10]=2[CH:17]=[CH:16][C:15]=1[CH2:18][O:19][C:22](=[O:23])[C:24]([F:27])([F:26])[F:25]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 687152574-Methoxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

Product 1

HCID 687123574-Methoxy-3-methyl-5-(2,2,2-trifluoro-acetoxymethyl)-benzofuran-2-carboxylic acid

Procedure

To 190 mg of 4-methoxy-5-hydroxymethyl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 4 mL of TFA/dichloromethane (1:1) and the solution was stirred at room temperature for 3 h. When the reaction was done, the solvents were removed under vacuum and the residue was triturated with acetonitrile. Filtration of the suspension gave 184 mg of 4-methoxy-3-methyl-5-(2,2,2-trifluoro-acetoxymethyl)-benzofuran-2-carboxylic acid as a white solid.

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was triturated with acetonitrile
  3. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-9f963e3b67a54dcf9c394a5c2746fce0
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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