Oxygen → 2-[4-(4-Methoxy-phenoxy)-phenyl]-[1,3,4]oxadiazole

HRID 49148Notes

Reaction equation

HRID 49148 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[O:12]1[CH:16]=[N:15][N:14]=[C:13]1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(N(CC)CC)C.O=O>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:23][C:20]2[CH:19]=[CH:18][C:17]([C:13]3[O:12][CH:16]=[N:15][N:14]=3)=[CH:22][CH:21]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 977OxygenHCID 8471TriethylamineHCID 201262(4-Methoxyphenyl)boronic acidHCID 7147704-(1,3,4-Oxadiazol-2-yl)phenol

Product 1

HCID 206362342-[4-(4-Methoxy-phenoxy)-phenyl]-[1,3,4]oxadiazoleYield 72.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-methoxybenzeneboronic acid (1.9 g, 12 mmol), 4-(1,3,4)oxadiazol-2-yl-phenol (1.0 g, 6.2 mmol), copper(II)acetate (1.1 g, 6.2 mmol), crushed 4-Angstrom molecular sieves (0.65 g), triethylamine (4.2 mL) and methylene chloride (22.7 mL) was stirred under 1 atm of oxygen gas for 48 hours. The mixture was filtered through a pad of Celite®, concentrated in vacuo and purified by radial chromatography (2:1 hexane-ethyl acetate), affording 1.2 g of 2-[4-(4-Methoxy-phenoxy)-phenyl]-[1,3,4]oxadiazole.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. custompurified by radial chromatography (2:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c88edd41642443cb8969d2fea6ae17ea
Source dataset
uspto-grants-2004_03
Patent number
US06706723B2

Reaction notes

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