Sodium Carbonate → HCID 67170582, Verbindung

HRID 1475789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1475789
Br[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(=O)OCC.O.CN(C=O)C>[CH3:23][O:22][C:20]([C:17]1[CH:16]=[C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]3[CH2:11][O:10][CH2:9]3)[CH:3]=2)[C:14]([O:13][CH3:12])=[CH:19][CH:18]=1)=[O:21]

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 9837205(2-Methoxy-5-(methoxycarbonyl)phenyl)boronic acidHCID 534843193-(3-Bromophenyl)oxetane

Produkt 1

HCID 67170582HCID 67170582, VerbindungAusbeute 71,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1.3 g of 3-(3-bromo-phenyl)-oxetane, 1.3 g of 2-methoxy-5-methoxycarbonylphenylboronic acid, 1.3 g of Na2CO3, 69 mg of palladium(II)acetate, and 160 mg of triphenylphosphine were combined and 15 ml of DMF and 1 ml of water added. The mixture was stirred at 100° C. for 1 h and then allowed to cool to room temperature. 100 ml of EA were then added and washed three times using 30 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:3 yielded 1.3 g of the title compound, colorless oil.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed three times
  3. customThe organic layer was then dried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1fbd5366a2454335ac747888eb95d6e1
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018383B2

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