Imidazole → [(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

HRID 42843

Reaktionsgleichung

Reaktionsgleichung von HRID 42843
N#N.[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][OH:10])[S:7][CH:8]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>C(Cl)Cl.O>[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[S:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 947NitrogenHCID 28928tert-Butyldimethylsilyl chlorideHCID 2795484(4-Bromo-2-thienyl)methanol

Produkt 1

HCID 10614666[(4-Bromo-2-thienyl)methoxy]t-butyldimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), (4-bromo-thiophen-2-yl)-methanol (3.97 g, 20.57 mmol) was dissolved in dry CH2Cl2 (50 mL). tert-Butyldimethylsilyl chloride (3.59 g, 22.63 mmol) was added at rt followed by imidazole (1.56 g, 22.63 mmol). The reaction mixture was stirred at rt for 1 h. Water was added, the layers were separated and the org. layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (hept) gave the title compound as a colorless oil. TLC:rf (100:1 hept-EA)=0.44. LC-MS-conditions 02: tR=1.21 min.

Aufarbeitung

  1. customthe layers were separated
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customPurification of the residue by FC (hept)

Quellen und Nachweise

ORD-Eintrag
ord-0dabf680e16e480dbc3cf2edbb1477c1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536209B2

Verknüpfte Notizen

Wird geladen…