Imidazole → tert-Butyl(2-fluorophenethoxy)dimethylsilane

HRID 471170

Reaktionsgleichung

Reaktionsgleichung von HRID 471170
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][OH:18].N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[C:4]([Si:1]([O:18][CH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[F:9])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27332962-(2-Fluorophenyl)ethan-1-ol

Produkt 1

HCID 57988979tert-Butyl(2-fluorophenethoxy)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

tert-Butyldimethylsilyl chloride (6.45 g) was added to a stirred solution of 2-(2-fluorophenyl)ethanol (5.00 g) and 1H-imidazole (7.29 g) in dry DMF (30 mL) cooled in an ice bath. After 45 min, the reaction mixture was diluted with ethyl acetate, washed three times with water and evaporated in vacuo. The resulting gum was dissolved in isohexane and applied to a silica gel column eluting with isohexane followed by 1:3 ethyl acetate:isohexane to collect the product as an oil. Yield 9.0 g.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. washwashed three times with water
  3. customevaporated in vacuo
  4. dissolutionThe resulting gum was dissolved in isohexane
  5. washeluting with isohexane
  6. customisohexane to collect the product as an oil

Quellen und Nachweise

ORD-Eintrag
ord-75e7c65448fb44f4b8dc805bd90d4d62
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629271B2

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