Hydrochloric Acid → Prinaberel

HRID 491737

Reaktionsgleichung

Reaktionsgleichung von HRID 491737
C(=O)([O-])[O-].[K+].[K+].C([O:10][C:11]1[CH:12]=[C:13]([CH:31]=[CH2:32])[C:14]2[O:18][C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C(=O)C)=[C:21]([F:29])[CH:20]=3)=[N:16][C:15]=2[CH:30]=1)(=O)C.O1CCOCC1.Cl>O>[F:29][C:21]1[CH:20]=[C:19]([C:17]2[O:18][C:14]3[C:13]([CH:31]=[CH2:32])=[CH:12][C:11]([OH:10])=[CH:30][C:15]=3[N:16]=2)[CH:24]=[CH:23][C:22]=1[OH:25]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 112682632-[4-(Acetyloxy)-3-fluorophenyl]-7-vinyl-1,3-benzoxazol-5-yl acetate

Produkt 1

HCID 656954PrinaberelAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Potassium carbonate (55 mg) was added into a solution of 2-[4-(acetyloxy)-3-fluorophenyl]-7-vinyl-1,3-benzoxazol-5-yl acetate (0.14 g, 0.39 mmol) and 1,4-dioxane (3 mL). The mixture was stirred at 90° C. for 1 h, poured into water, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and crystallization from EtOAc/hexanes, gave a white solid (0.06 g, 46% yield, map. 250-252° C.); MS m/e 272 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and crystallization from EtOAc/hexanes
  4. customgave a white solid (0.06 g, 46% yield, map. 250-252° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f1b7c1b8c9784bb99dd8861ba5d6a964
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531564B2

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