Imidazole → tert-Butyl(4-fluorophenethoxy)dimethylsilane

HRID 446356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446356
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][OH:18])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C=O)C>[C:4]([Si:1]([O:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=1)([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 820684-Fluorophenethyl Alcohol

Produkt 1

HCID 57989254tert-Butyl(4-fluorophenethoxy)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

tert-Butyldimethylsilyl chloride (9.03 g) was added portionwise to a stirred solution of 2-(4-fluorophenyl)ethanol (7 g) and imidazole (4.08 g) in DMF (100 mL) at 20° C. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ethyl acetate and brine. The organic layer was washed twice with brine, dried, filtered and the solvent concentrated under reduced pressure. The crude product was purified by flash silica chromatography eluting with 2% ethyl acetate in isohexane. Fractions containing the product were evaporated to dryness to afford the subtitled compound. Yield 11.60 g.

Aufarbeitung

  1. custompartitioned between ethyl acetate and brine
  2. washThe organic layer was washed twice with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationthe solvent concentrated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 2% ethyl acetate in isohexane
  8. additionFractions containing the product
  9. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-45f25db98bde4694935f5f8058e04ce4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476265B2

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