Water → HCID 23359176, compound

HRID 232872Notes

Reaction equation

HRID 232872 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([O:17][C:18]1[CH:36]=[CH:35][C:21]([O:22][CH2:23][C:24]2[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:25]=2[C:26]([OH:28])=O)=[CH:20][CH:19]=1)(=[O:16])[CH3:15].O.[OH-].[Na+]>C(Cl)Cl>[C:14]([O:17][C:18]1[CH:19]=[CH:20][C:21]2[O:22][CH2:23][C:24]3[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:25]=3[C:26](=[O:28])[C:35]=2[CH:36]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 23359181HCID 23359181, compound

Product 1

HCID 23359176HCID 23359176, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 ml of trifluoroacetic anhydride and 0.48 g of a trifluoroboran-diethyl ether complex were added to 5.36 g of 2-(4-acetoxyphenoxy)methyl-4-cyanobenzoic acid obtained in Reference example 24 dissolved in 80 ml of methylene chloride and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction mixture, the mixture was neutralized with a 1N-sodium hydroxide aqueous solution and crystals precipitated were extracted with chloroform. Then, the organic layer was dried over anhydrous sodium sulfate and the residue obtained by removing the solvent was applied to silica gel column chromatography to obtain 2.8 g of the title compound.

Workup

  1. customobtained in Reference example 24
  2. customprecipitated
  3. extractionwere extracted with chloroform
  4. dry with materialThen, the organic layer was dried over anhydrous sodium sulfate
  5. customthe residue obtained
  6. customby removing the solvent

Sources & evidence

ORD record
ord-90cebd774a014d7f8d306e91b100402c
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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