Imidazole → HCID 21875145, Verbindung

HRID 723645

Reaktionsgleichung

Reaktionsgleichung von HRID 723645
[CH3:1][C:2]1[O:6][C:5]([CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(OCC)C>CN(C=O)C>[CH3:19][C:18]([Si:15]([CH3:17])([CH3:16])[O:9][CH2:8][CH2:7][C:5]1[O:6][C:2]([CH3:1])=[CH:3][CH:4]=1)([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 110623902-(5-Methylfuran-2-yl)ethan-1-ol

Produkt 1

HCID 21875145HCID 21875145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 21A (2.00 g, 15.9 mmol) in DMF (50 mL) was added imidazole (1.62 g, 23.9 mmol), followed by tert-butyldimethylsilyl chloride (2.63 g, 17.5 mmol). After 2 h at 25° C., the reaction was poured into diethyl ether (300 mL) and washed with water (1×100 mL), 1 N HCl (1×100 mL), water (1×100 mL), brine (1×50 mL) and dried over anhydrous MgSO4. Crude compound 204A was analyzed by LCMS and NMR and determined to be pure enough to be carried on directly to the next step. HPLC: 100% at 4.347 min (retention time) (YMC S5 ODS column 4.6×50 mm eluting with 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm).

Aufarbeitung

  1. washwashed with water (1×100 mL), 1 N HCl (1×100 mL), water (1×100 mL), brine (1×50 mL)
  2. dry with materialdried over anhydrous MgSO4
  3. washHPLC: 100% at 4.347 min (retention time) (YMC S5 ODS column 4.6×50 mm eluting with 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm)

Quellen und Nachweise

ORD-Eintrag
ord-26cd1984d7004fcc8455fb15024fd940
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141578B2

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