2-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanol → 4-{4-[2-(2-Hydroxy-ethyl)-imidazol-1-ylmethyl]-oxazol-2-yl}-phenol

HRID 854695Notes

Reaction equation

HRID 854695 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH2:26][CH2:27][OH:28])[N:19]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[OH:28][CH2:27][CH2:26][C:22]1[N:21]([CH2:20][C:18]2[N:19]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[O:16][CH:17]=2)[CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 1

HCID 694248212-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanol

Product 1

HCID 1363517344-{4-[2-(2-Hydroxy-ethyl)-imidazol-1-ylmethyl]-oxazol-2-yl}-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.90 g (2.39 mmol) 2-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanol in 60 ml THF was hydrogenated for 2 hours over 250 mg 10% Pd/C at ambient temperature and pressure. After filtration, the solvent was evaporated to leave 0.55 g (80%) 4-{4-[2-(2-hydroxy-ethyl)-imidazol-1-ylmethyl]-oxazol-2-yl}-phenyl as light yellow crystals.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was evaporated
  3. customto leave 0.55 g (80%) 4-{4-[2-(2-hydroxy-ethyl)-imidazol-1-ylmethyl]-oxazol-2-yl}-phenyl as light yellow crystals

Sources & evidence

ORD record
ord-3ed934d386ff4194807aab94fec91c5c
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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