Tetrabutylammonium Fluoride → 1,5-Naphthyridine

HRID 1587831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587831
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si](OCCO[C:40]1[N:41]=[C:42]2[C:47](=[CH:48][CH:49]=1)[N:46]=[C:45](CC)[CH:44]=[C:43]2OCC1C=CC(C2C=CC=CC=2C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[N:41]1[C:42]2[C:47](=[N:46][CH:45]=[CH:44][CH:43]=2)[CH:48]=[CH:49][CH:40]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 53976296HCID 53976296, Verbindung

Produkt 1

HCID 1360701,5-NaphthyridineAusbeute 550,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A 1M solution of tetrabutylammonium fluoride in THF (14 ml) was added to a solution of compound E (1.1 g) in THF (10 ml) and the mixture was stirred for 2 hours. The solution was then warmed to 40° C. for 10 minutes. Volatile material was removed by evaporation and the residual oil was dissolved in ethyl acetate (75 ml) and washed with water (75 ml and 30 ml). The precipitated solid was collected by filtration to give 2-ethyl-6-hydroxy-4-[(2'-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)-methoxy]-1,5-naphthyridine (F) (0.83 g) as a white solid, m.p. 148°-149° C.; NMR (d6 -DMSO): 1.2(t,3H), 2.7(q,2H), 5.3(s,2H), 6.65-7.9(m,26H), 11.1(s,1H).

Aufarbeitung

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residual oil was dissolved in ethyl acetate (75 ml)
  3. washwashed with water (75 ml and 30 ml)
  4. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-b895d3e606f14bfa9666ce126eb04785
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219863

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