Ethyl Acetate → Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

HRID 557819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557819
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>O.C1(C)C=CC=CC=1.C(O)C.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>[C:22]1([C:8]2[N:13]=[CH:12][C:11]([C:14]3([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

Produkt 1

HCID 66661635Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Sodium carbonate (42.4 mg, 0.400 mmol) in water (0.20 mL) was added to a mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.200 mmol), Phenylboronic acid (24.4 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.15 mg) in toluene (200.0 μL) and ethanol (100.0 μL). The resulting mixture was irradiated by microwave at 120° C. for 15 minutes. Ethyl acetate (5 mL) was then added to the mixture. The resulting mixture was washed with water followed by brine. The organic layer was dried over Na2SO4, then filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate/hexane to give ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate.

Aufarbeitung

  1. customThe resulting mixture was irradiated by microwave at 120° C. for 15 minutes
  2. washThe resulting mixture was washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-32961ba308614a839d8e3bb0a38a77c9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058288B2

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