Imidazole → tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane

HRID 1689433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689433
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][OH:24]>CN(C=O)C.C(OCC)(=O)C>[C:4]([Si:1]([O:24][CH2:23][CH2:22][CH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[F:14])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 126185173-(2-Fluorophenyl)propan-1-ol

Produkt 1

HCID 57989116tert-Butyl(3-(2-fluorophenyl)propoxy)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyldimethylsilyl chloride (3.19 g) was added to a solution of imidazole (3.6 g) and 3-(2-fluorophenyl)propan-1-ol (example 88, step a) (2.72 g) in dry DMF (30 mL) cooled in an ice bath. After 45 min, the reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×100 mL) and evaporated. The resulting gum was purified by silica gel chromatography eluting with isohexane. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 4.4 g.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. washwashed with water (3×100 mL)
  3. customevaporated
  4. customThe resulting gum was purified by silica gel chromatography
  5. washeluting with isohexane
  6. additionThe fractions containing product
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c77374674e624663add1fd75da032dd4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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