Acetonitrile → Prinaberel

HRID 1007346

Reaktionsgleichung

Reaktionsgleichung von HRID 1007346
F.[Si]([O:9][C:10]1[CH:11]=[C:12]([CH:34]=[CH2:35])[C:13]2[O:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][Si](C(C)(C)C)(C)C)=[C:20]([F:32])[CH:19]=3)=[N:15][C:14]=2[CH:33]=1)(C(C)(C)C)(C)C.C1COCC1.C(#N)C>O>[F:32][C:20]1[CH:19]=[C:18]([C:16]2[O:17][C:13]3[C:12]([CH:34]=[CH2:35])=[CH:11][C:10]([OH:9])=[CH:33][C:14]=3[N:15]=2)[CH:23]=[CH:22][C:21]=1[OH:24]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8028TetrahydrofuranHCID 14917Hydrofluoric AcidHCID 597416385-(Tert-butyl-dimethyl-silanyloxy)-2-[4-(tert-butyl-dimethyl-silanyloxy)-3-fluoro-phenyl]-7-vinyl-benzooxazole

Produkt 1

HCID 656954PrinaberelAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Hydrofluoric acid (48 wt. % in water, 1 mL) was added into a solution of 5-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-{[tert-butyl(dimethyl)silyl]oxy}-3-fluorophenyl)-7-vinyl-1,3-benzoxazole (1.5 g, 3.0 mmol), THF (6 mL) and acetonitrile (3 mL). The reaction mixture was stirred at 65° C. for 8 h, and then poured into water. The precipitated solid was filtered off and dried. Crystallization of the product from acetone/ethyl ether gave a white solid (0.72 g, 81% yield, m.p. 249-251° C.); MS m/e 272 (M+H)+.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered off
  2. customdried
  3. customCrystallization of the product from acetone/ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-bf261d8c914a474eb6cebb22e8770f87
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794403B2

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