tert-Butyldiphenylchlorosilane → 4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

HRID 242386

Reaktionsgleichung

Reaktionsgleichung von HRID 242386
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[CH:8]1.[CH3:16][C:17]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])[CH3:18]>ClCCl.CN(C1C=CN=CC=1)C>[Si:20]([O:13][CH2:12][C:10]1[N:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 94078tert-ButyldiphenylchlorosilaneHCID 695583761-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol

Produkt 1

HCID 710872934-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(2-Trimethylsilylethoxymethyl)-1H-imidazole-4-methanol (100 g) was dissolved in dichloromethane (1 L), and under stirring TEA (122 mL), DMAP (5.35 g), and then TBDPSCl (149 mL) were added. After stirring for 1 day, the reaction mixture solution was washed with water, 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=25%-50%) using silica gel column (product name: Ultra Pack E, manufactured by Yamazen Corporation) to afford the title compound (146 g).

Aufarbeitung

  1. washthe reaction mixture solution was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationsubsequently the solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=25%-50%)

Quellen und Nachweise

ORD-Eintrag
ord-0740e4e2a6d74c7680fc97aab1e42bee
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653126B2

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