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

HRID 471203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 471203
[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-4cdee596ed684782abbec5ff149bb809
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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