HCID 18700175, compound → HCID 18700130, compound

HRID 2289346Notes

Reaction equation

HRID 2289346 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:11]([O:20][CH2:21][C:22]([F:23])([F:24])[F:25])[CH:10]=1

Participants

4

Reactant 1

HCID 18700175HCID 18700175, compound

Product 1

HCID 18700130HCID 18700130, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-benzyloxy-2-(2,2,2-trifluoroethoxy)phenylacetate from Step 3 in MeOH was added palladium black (250 mg). The mixture was stirred under an atmosphere of hydrogen gas (1 atm) for 3 h. The hydrogen was removed by bubbling argon through the mixture for 10 min, and the catalyst was removed by filtration. The filtrate solvents were removed inder reduced pressure and the residue was purifed by pressurized silica gel column chromatography using 1:3 EtOAc:hexanes as eluant to give methyl 4-hydroxy-2-(2,2,2-trifluoroethoxy)phenylacetate as a solid (HPLC retention time=18.1 min (method D)).

Workup

  1. customThe hydrogen was removed
  2. customby bubbling argon through the mixture for 10 min
  3. customthe catalyst was removed by filtration
  4. customThe filtrate solvents were removed inder reduced pressure

Sources & evidence

ORD record
ord-7efa795663bc4ec5bad27ae58a30c3d0
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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