Imidazole → 2-[(Tert-butyldimethylsilyloxy)methyl]benzylalcohol

HRID 578799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 578799
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[Si:20]([O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 691531,2-Benzenedimethanol

Produkt 1

HCID 108484452-[(Tert-butyldimethylsilyloxy)methyl]benzylalcoholAusbeute 41,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1,2-benzenedimethanol (2 g) and imidazole (1.13 g) in N,N-dimethylformamide (30 mL) was added tert -butyldimethylchlorosilane (2.08 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2) to give the title compound (1.46 g).

Aufarbeitung

  1. washthe resulting mixture was washed with 1 mol/L hydrochloric acid, water and brine successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=3/2)

Quellen und Nachweise

ORD-Eintrag
ord-42fc0e5b916744c58986e36b2fa15a33
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040693B2

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