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

HRID 1824822Notes

Reaction equation

HRID 1824822 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[CH2:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=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-35541ccbccaf46229d9dc7c5718d5a66
Source dataset
uspto-grants-2006_05
Patent number
US07045541B2

Reaction notes

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