Potassium Carbonate → HCID 68465652, Verbindung

HRID 1927737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1927737
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][C:23]1[CH:40]=[CH:39][C:26]([CH2:27][CH2:28][NH:29][C:30](=[O:38])[C:31]2[CH:36]=[CH:35][C:34](F)=[CH:33][CH:32]=2)=[CH:25][CH:24]=1>CS(C)=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH2:28][NH:29][C:30]([C:31]2[CH:32]=[CH:33][C:34]([O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:7]=3)=[CH:35][CH:36]=2)=[O:38])=[CH:39][CH:40]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 737426HCID 737426, VerbindungHCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetate

Produkt 1

HCID 68465652HCID 68465652, VerbindungAusbeute 4,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Tert-butyl 2-(4-hydroxyphenyl)acetate (200 mg, 0.960 mmol) was diluted with DMSO (4 mL) followed by the addition of K2CO3 (133 mg, 0.960 mmol) and N-(4-chlorophenethyl)-4-fluorobenzamide (267 mg, 0.960 mmol). The reaction was stirred at 85° C. overnight, and then stirred at 138° C. for 12 hours. The reaction was cooled to ambient temperature, diluted with DCM and 10% aq. sodium carbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (4:1) to yield tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)phenyl)acetate (20 mg, 4.47% yield) as an off white solid.

Aufarbeitung

  1. stirringstirred at 138° C. for 12 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f3215438f70c4da187d867366b74820a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08183289B2

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