Trifluoroacetic acid → 4-(4-(2,6-Difluorobenzyloxy)phenyl)-4-oxobutyric acid

HRID 25005Notes

Reaction equation

HRID 25005 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=2[F:26])=[CH:13][CH:12]=1)=[O:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:25][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([F:26])[C:19]=1[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[CH2:8][CH2:7][C:6]([OH:27])=[O:5])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21964483tert-Butyl 4-(4-(2,6-difluorobenzyloxy)phenyl)-4-oxobutyrate

Product 1

HCID 121322974-(4-(2,6-Difluorobenzyloxy)phenyl)-4-oxobutyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl 4-(4-(2,6-difluorobenzyloxy)phenyl)-4-oxobutyrate (Step B, 4.76 g, 12.6 mmol) in dichloromethane (40 ml) was treated with trifluoroacetic acid (20 ml). The mixture was stirred at ambient temperature for 3 hours and concentrated in vacuo. The purification was done by flash chromatography on silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to provide the title compound as a white powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe purification

Sources & evidence

ORD record
ord-4512b058013348ea9ea62316bb4016fa
Source dataset
uspto-grants-2005_02
Patent number
US06858602B2

Reaction notes

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