Cesium carbonate → HCID 66653882, Verbindung

HRID 571784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571784
[CH2:1]([N:8]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([S:27]([O-:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+].C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCOC(C)=O>[C:21]1([S:27]([C:17]2[CH:18]=[CH:19][C:14]([CH:12]3[O:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:13]3)=[CH:15][CH:16]=2)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

10

Edukt 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

Produkt 1

HCID 66653882HCID 66653882, VerbindungAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a degassed mixture of 4-benzyl-6-(4-bromo-phenyl)-morpholine (0.45 g; 1.35 mmol), sodium benzenesulfinate (0.27 g; 1.63 mmol), Cs2CO3 (0.66 g; 2.03 mmol), and tetrabutylammonium chloride (0.45 g; 1.63 mmol) in toluene (10 mL), was added Pd2dba3 (31.01 mg; 0.03 mmol) and Xantphos (39.19 mg; 0.07 mmol). The resulting mixture was heated under reflux for 2 days. After cooling to RT, EtOAc and a 5% aqueous NaHCO3 solution were added. The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O) to afford 2-(4-benzenesulfonyl-phenyl)-4-benzyl-morpholine (0.28 g).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 days
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2, Et2O)

Quellen und Nachweise

ORD-Eintrag
ord-9025dc6a3dae4a77b4190ca4a01031d0
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029371B2

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