Chlorotriethylsilane → 1-Ethoxymethyl-4-(triethylsilyloxymethyl)-1H-imidazole

HRID 242370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242370
[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][OH:11])[N:7]=[CH:6]1)[CH3:2].[CH2:12]([Si:14](Cl)([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13]>ClCCl.CN(C1C=CN=CC=1)C.O>[CH2:1]([O:3][CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][O:11][Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:12][CH3:13])[N:7]=[CH:6]1)[CH3:2]

Komponenten

6

Edukt 2

HCID 13819ChlorotriethylsilaneHCID 682713641-Ethoxymethyl-1H-imidazole-4-methanol

Produkt 1

HCID 710871261-Ethoxymethyl-4-(triethylsilyloxymethyl)-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (520 mg) obtained in (2) was dissolved in dichloromethane (30 mL), followed by addition of triethylsilyl chloride (1.12 mL), TEA (1.16 mL) and DMAP (catalytic amount) under stirring, and the stirring was continued for 17 hours. The reaction solution was diluted with water, and extracted with chloroform. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→80%) using silica gel column (product name: SNAP Cartridge KP-Sil 50 g, manufactured by Biotage, Ltd.) to afford the title compound (665 mg).

Aufarbeitung

  1. extractionextracted with chloroform
  2. extractionThe combined extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationsubsequently the solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→80%)

Quellen und Nachweise

ORD-Eintrag
ord-cb1d220ce0b448339ed7b40c8f9dd220
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653126B2

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