Hydrochloric Acid → HCID 11384598, Verbindung

HRID 1869288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869288
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[O:10][C:6]=2[C:5]([O:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:4][CH:3]=1.[CH2:23]([N:25]([CH2:31][CH3:32])[C:26](=[O:30])/[CH:27]=[CH:28]/[CH3:29])[CH3:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:9]1[O:10][C:6]2[C:5]([O:14][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[CH:4][CH:3]=[C:2](/[C:28](/[CH3:29])=[CH:27]/[C:26]([N:25]([CH2:31][CH3:32])[CH2:23][CH3:24])=[O:30])[C:7]=2[CH:8]=1)(=[O:13])[CH3:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 80271Tri-o-tolylphosphineHCID 53544532-ButenaMide, N,N-diethyl-, (E)-HCID 113143551-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone2×

Produkt 1

HCID 11384598HCID 11384598, VerbindungAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
84 °C

Versuchsvorschrift

1-[4-Bromo-7-(1-phenylethoxy)benzofuran-2-yl]ethanone (compound 3) (1.0 g, 2.79 mmol) and (E)-N,N-diethyl-2-butenamide (0.47 g, 3.35 mmol) were dissolved in triethylamine (10 ml), and the inside of the system was replaced by nitrogen gas. Palladium acetate (0.031 g, 0.14 mmol) and tri-o-tolylphosphine (0.085 g, 0.28 mmol) were added and the mixture was stirred with heating at 78-90° C. for 16 hr. After confirmation of the completion of the reaction by TLC, 5% HCl aqueous solution was added and the mixture was extracted with ethyl acetate. The mixture was washed with saturated brine, dried over MgSO4, and the solvent was evaporated to give a brown oil. Purification by silica gel column chromatography (hexane:acetone=5:1) was performed to give (E)-3-[2-acetyl-7-(1-phenylethoxy)benzofuran-4-yl]-N,N-diethyl-2-butenamide (0.51 g, yield 43.6%) as a pale-yellow crystal.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe mixture was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated
  6. customto give a brown oil
  7. customPurification by silica gel column chromatography (hexane:acetone=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-19e8944c48184a8eb325e2d9537b6e81
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638540B2

Notizen zur Reaktion

Wird geladen…