Imidazole → 4-((Triisopropylsilyloxy)methyl)thiazole

HRID 2071064

Reaktionsgleichung

Reaktionsgleichung von HRID 2071064
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.[CH3:8][CH:9]([Si:11](Cl)([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH3:10].N1C=CN=C1>C(Cl)Cl>[CH:9]([Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:14])[CH3:13])[O:7][CH2:6][C:4]1[N:3]=[CH:2][S:1][CH:5]=1)([CH3:10])[CH3:8]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 2763215(1,3-Thiazol-4-yl)methanol

Produkt 1

HCID 686703364-((Triisopropylsilyloxy)methyl)thiazoleAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a DCM solution of thiazol-4-ylmethanol (Combi-Blocks)(1 g, 8.69 mmol) stirred at 0° C., were added TIPSCl (2.2 mL, 10.43 mmol) and imidazole (1.48 g, 21.72 mmol). The resulting mixture was then warmed to room temperature and stirred for overnight. The reaction was quenched with saturated aqueous NH4Cl solution, extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, concentrated to a residue which was purified by flash column to give 4-((triisopropylsilyloxy)methyl)thiazole (2 g). 1H NMR (300 MHz, CDCl3), d: 8.794 (m, 1H), 7.338 (m, 1H), 5.065 (s, 2H), 1.209 (m, 3H), 1.133 (d, J=6 Hz, 18H).

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NH4Cl solution
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated to a residue which
  6. customwas purified by flash column

Quellen und Nachweise

ORD-Eintrag
ord-d1897134dd9a41cca40357542317dec7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299267B2

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