Tetrabutylammonium Fluoride → HCID 136249894, Verbindung

HRID 2222274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222274
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6]1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH:5]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[CH:6]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 693030142-{1-[Tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}-1,3-thiazole

Produkt 1

HCID 136249894HCID 136249894, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]-1,3-thiazole (0.200 g, 0.671 mmol) in anhydrous THF (2 mL) was added TBAF (1 mL, 1 mmol of a 1M in THF) and after stirring for 20 min at rt, the reaction was complete. The reaction mixture was quenched with water (40 mL), extracted with EtOAc (3×25 mL) and washed with brine. The organic phase was dried over Na2SO4, concentrated in vacuo and chromatographed on silica gel eluting with EtOAc:hexane (1:1) to afford 2-(1H-pyrrol-3-yl)-1,3-thiazole as a pale solid. 1H NMR (CD3Cl, 300 MHz) δ 8.20 (br, 1H) 7.63 (d, 1H), 7.28 (d, 1H), 7.06 (d, 1H), 6.73 (dd, 1H), 6.57 (dd, 1H).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (40 mL)
  2. extractionextracted with EtOAc (3×25 mL)
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel eluting with EtOAc:hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-8cf5be524bb24b278a514d60e294b1c7
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371767B2

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