Ammonium formate → 5-Fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl]phenol

HRID 741795Notes

Reaction equation

HRID 741795 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]([OH:24])([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[CH2:17][CH3:18])[CH:5]=[C:6]([O:8]CC2C=CC=CC=2)[CH:7]=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:16]([OH:24])([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[CH2:17][CH3:18])[CH:5]=[C:6]([OH:8])[CH:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 199096325-fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl](O-benzyl)phenol

Product 1

HCID 194270045-Fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl]phenolYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-fluoro-3-[1-hydroxy-1-(thiazol-2-yl)propyl](O-benzyl)phenol (200 mg, 0.58 mmol) in MeOH (9 mL) was added 10% Pd on charcoal (200 mg) and ammonium formate (180 mg, 2.9 mmol). The reaction mixture was refluxed for 2 h and then flitrated through a pad of celite and washed with EtOAc. After evaporation of the solvent, the residue was purified by chromatography on silica gel using a mixture of hexane:EtOAc 7:3 to give 116 mg (79%) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. washwashed with EtOAc
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by chromatography on silica gel using
  5. additiona mixture of hexane:EtOAc 7:3

Sources & evidence

ORD record
ord-f8b672d1eefe46f9bb0319a3f52dad41
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

Loading…