Toluene → HCID 11759644, Verbindung

HRID 350705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350705
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.OB(O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+].C1(C)C=CC=CC=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.O.C(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:3][C:4]=2[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:9]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 10990225Methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate

Produkt 1

HCID 11759644HCID 11759644, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-[2-chloro-4-(4-chlorophenyl)-5-oxazolyl]propionate (1.50 g), dihydroxyphenylborane (650 mg), sodium hydrogen carbonate (1.68 g), tetrakis(triphenylphosphine)palladium (250 mg), toluene (50 mL), ethanol (25 mL) and water (25 mL) was stirred under an argon atmosphere with heating under reflux for 12 hrs. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography. Methyl 3-[4-(4-chlorophenyl)-2-phenyl-5-oxazolyl]propionate (1.50 g, 88%) was obtained as a yellow oil from a fraction eluted with hexane-ethyl acetate (6:1, volume ratio).

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 12 hrs
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-870c270575df402ab1f8d95cc4283304
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183276B2

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