Water → HCID 10665616, compound

HRID 1108048Notes

Reaction equation

HRID 1108048 reaction equation
C([O:8][CH2:9][CH2:10][S:11][C:12]([F:30])([F:29])[C:13]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])([OH:20])[CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)C1C=CC=CC=1.[H][H].O>C(O)C.[Pd]>[F:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[C:13]([OH:20])([CH2:14][N:15]1[CH:19]=[N:18][CH:17]=[N:16]1)[C:12]([F:30])([F:29])[S:11][CH2:10][CH2:9][OH:8]

Participants

6

Reactant 3

HCID 962WaterHCID 18786630HCID 18786630, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10665616HCID 10665616, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-benzyloxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (1.0 g, 2.2 mmol) in ethanol (20 ml), palladium black (20 mg, catalytic) was added, followed by stirring at room temperature and 1 atmospheric pressure in a hydrogen gas for 12 hours. After the completion of the reaction, an insoluble matter was filtered off. The solvent was then distilled off under reduced pressure. To the residue so obtained, water was added, followed by extraction with chloroform. The chloroform solution was washed with water, dried over magnesium sulfate and then distilled off under reduced pressure. To the residue, isopropyl ether was added for crystallization, whereby 2-(2,4-difluorphenyl)-1,1-difluoro-1-(2-hydroxyethyl)thio-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (0.46 g, yield: 55.0%) was obtained as colorless crystals.

Workup

  1. customAfter the completion of the reaction
  2. filtrationan insoluble matter was filtered off
  3. distillationThe solvent was then distilled off under reduced pressure
  4. customTo the residue so obtained
  5. extractionfollowed by extraction with chloroform
  6. washThe chloroform solution was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationdistilled off under reduced pressure
  9. additionTo the residue, isopropyl ether was added for crystallization

Sources & evidence

ORD record
ord-6e404f4223374a12a6e2222cde606668
Source dataset
uspto-grants-2000_05
Patent number
US06063945

Reaction notes

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