2-(4-Iodophenyl)oxazole → 2-[4-[(4-Methoxyphenyl)methyl]phenyl]oxazole

HRID 630339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630339
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[Cl-].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][Zn+])=[CH:18][CH:17]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][CH:10]=[CH:11][N:12]=3)=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 98602582-(4-Iodophenyl)oxazoleHCID 178490612HCID 178490612, Verbindung

Produkt 1

HCID 684889492-[4-[(4-Methoxyphenyl)methyl]phenyl]oxazoleAusbeute 81,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

C A Schlenk Flask was charged with tetrakis(triphenylphosphine)palladium(0) (0.42 g, 0.37 mmol), nitrogen, THF (20 ML), 2-(4-iodophenyl)oxazole (1 g, 3.7 mmol), and 4-methoxybenzyl zinc chloride (0.5 M in THF, 9.6 mL, 4.8 mmol). After 3 hours, the filtrate was concentrated. The resulting solid was treated with a mixture of ethyl acetate and a dilute aqueous ammonium chloride solution. The mixture was filtered and the organic layer was dried and concentrated. Purification on silica gel using a gradient of dichloromethane in hexane gave 0.8 g of 2-[4-[(4-methoxyphenyl)methyl]phenyl]oxazole, 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.22 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 3.96 (s, 2H), 3.78 (s, 3H).

Aufarbeitung

  1. concentrationthe filtrate was concentrated
  2. additionThe resulting solid was treated with a mixture of ethyl acetate
  3. filtrationThe mixture was filtered
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customPurification on silica gel using a gradient of dichloromethane in hexane

Quellen und Nachweise

ORD-Eintrag
ord-662338121f984e659df198bf7b90b661
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315509B2

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