Phenol → 4-(2-Benzyloxy-ethyl)-5-methyl-2-(4-phenoxy-phenyl)-oxazole

HRID 1181027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181027
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20](Br)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:30][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 996PhenolHCID 62657Potassium Phosphate, TribasicHCID 179843944-[2-(Benzyloxy)ethyl]-2-(4-bromophenyl)-5-methyl-1,3-oxazole

Produkt 1

HCID 179843804-(2-Benzyloxy-ethyl)-5-methyl-2-(4-phenoxy-phenyl)-oxazoleAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 27342152-(Di-tert-butylphosphino)biphenylKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-(2-benzyloxy-ethyl)-2-(4-bromo-phenyl)-5-methyl-oxazole (0.025 mol, 9.2 g), phenol (0.03 mol, 2.8 g), K3PO4 (0.05 mol, 10.6 g), 2-(di-tert-butylphosphino)biphenyl (1.8 mmol, 0.54 g) and Pd(OAc)2 (1.2 mmol, 0.28 g) in toluene (350 mL) was degassed with nitrogen and heated at 100° C. for 18 h. Additional Pd(OAc)2 (0.5 g) and phosphine ligand (1.0 g) were added, and the mixture was heated 5 h at 100° C. The reaction was concentrated and purified directly by silica gel chromatography (4/1 hexanes/ethyl acetate) to give the title compound (7.6 g).

Aufarbeitung

  1. customwas degassed with nitrogen
  2. additionAdditional Pd(OAc)2 (0.5 g) and phosphine ligand (1.0 g) were added
  3. temperaturethe mixture was heated 5 h at 100° C
  4. concentrationThe reaction was concentrated
  5. custompurified directly by silica gel chromatography (4/1 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-f1fdd23f8ce04eb0af12911dd06f6bdf
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282501B2

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