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Ethyl Acetate → 8-vinyl-3,4-dihydro-1H-1-benzazepine-2,5-dione

HRID 1672187
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1672187
I[C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[F-].[K+].[CH2:17]([Sn](CCCC)(CCCC)C=C)[CH2:18]CC.CCOC(C)=O>CN(C=O)C.[Cu]I.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>[CH:17]([C:2]1[CH:14]=[CH:13][C:5]2[C:6](=[O:12])[CH2:7][CH2:8][C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1)=[CH2:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 522689Potassium Fluoride2×HCID 584766238-iodo-2,3,4,5-tetrahydro-1H-1-benzazepine-2,5-dione

Produkt 1

HCID 673365978-vinyl-3,4-dihydro-1H-1-benzazepine-2,5-dioneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a degassed solution of 8-iodo-3,4-dihydro-1H-1-benzazepine-2,5-dione (0.3 g, 1.0 mmol) in DMF (5 mL) was added CuI (19 mg, 0.1 mmol), KF (116 mg, 2.0 mmol), tributylethenylstannane (0.58 mL, 2.0 mmol), and Pd(PPh3)4 (116 mg, 0.1 mmol). The reaction mixture was allowed to stir at 100° C. for 4 h. After being allowed to cool to rt, EtOAc (50 mL) and a 1M aqueous KF solution (25 mL) were added and the mixture was allowed to stir for an additional 40 min. The mixture was filtered over Celite® and the organic solution was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was treated with n-pentane and filtered. The resulting solid was purified by column chromatography to provide 8-vinyl-3,4-dihydro-1H-1-benzazepine-2,5-dione (80 mg, 40%).

Aufarbeitung

  1. temperatureto cool to rt
  2. stirringto stir for an additional 40 min
  3. filtrationThe mixture was filtered over Celite®
  4. customthe organic solution was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. additionThe residue was treated with n-pentane
  10. filtrationfiltered
  11. customThe resulting solid was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-39fb4b9a21d54ea0867b6436f8073f72
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998952B2

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