HCID 19608673, compound → HCID 19608677, compound

HRID 1603073Notes

Reaction equation

HRID 1603073 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH:21]=[N:20][N:19]=[CH:18]2)=[CH:13][CH:12]=1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)(=O)C>[N:19]1[N:20]=[CH:21][N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][OH:8])=[CH:16][CH:15]=2)[CH:18]=1

Participants

5

Reactant 2

HCID 19608673HCID 19608673, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19608677HCID 19608677, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-[4-(2-benzyloxyethyl)phenyl]-4H-[1,2,4]triazole (0.237 g in 20 mL methanol) was added 183 mg of 10% palladium hydroxide on carbon catalyst followed by 0.20 mL acetic acid. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 11 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:7:1) gave the title compound (0.147 g).

Workup

  1. customevacuated
  2. customAfter 11 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (methylene chloride:methanol:ammonium hydroxide, 90:7:1)

Sources & evidence

ORD record
ord-42486261092547c8bf4e34f97b10af0e
Source dataset
uspto-grants-1999_11
Patent number
US05985901

Reaction notes

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