Toluene → HCID 67361124, Verbindung

HRID 1909093

Reaktionsgleichung

Reaktionsgleichung von HRID 1909093
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]2([CH3:15])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)=[CH:4][CH:3]=1.[F:18][C:19]([F:35])([F:34])[O:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:23][CH:22]=1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O.C(OCC)(=O)C>[F:35][C:19]([F:18])([F:34])[O:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]2[CH2:27][CH2:28][N:29]([C:2]3[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]4([CH3:15])[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]4)=[CH:4][CH:3]=3)[CH2:30][CH2:31]2)=[CH:23][CH:22]=1

Komponenten

9

Edukt 4

HCID 1140TolueneHCID 161154394-[4-(Trifluoromethoxy)phenoxy]piperidineHCID 23676156Sodium t-butoxideHCID 710593314-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane

Produkt 1

HCID 67361124HCID 67361124, VerbindungAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 86674235Tri-tert-butylphosphine tetraphenylborateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane (156 mg, 0.518 mmol), 4-[4-(trifluoromethoxy)phenoxy]piperidine (135 mg, 0.517 mmol), palladium acetate (1.2 mg, 0.0053 mmol), tri-tert-butylphosphine tetraphenylborate (2.7 mg, 0.0052 mmol), sodium tert-butoxide (55 mg, 0.57 mmol), and toluene (2 mL) were mixed and stirred under reflux for 2 hours. Ethyl acetate and water were added to the reaction mixture, followed by extraction. The organic layer was washed with water twice. A residue was obtained by concentrating the organic layer under reduced pressure, and the resulting residue was then subjected to chromatography refining (methylene chloride) using silica gel, obtaining 232 mg of the objective compound (yield: 93%).

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. extractionfollowed by extraction
  3. washThe organic layer was washed with water twice
  4. customA residue was obtained
  5. concentrationby concentrating the organic layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d3bee796665b41afb7076e2b8902854f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598358B2

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