Imidazole → N-(2-((tert-butyldimethylsilyl)oxy)ethyl)aniline

HRID 63651

Reaktionsgleichung

Reaktionsgleichung von HRID 63651
[C:1]1([NH:7][CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl.O>[Si:20]([O:10][CH2:9][CH2:8][NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 31235N-(2-Hydroxyethyl)aniline

Produkt 1

HCID 21993569N-(2-((tert-butyldimethylsilyl)oxy)ethyl)anilineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(phenylamino)ethan-1-ol (2.0 g, 14.6 mmol) and imidazole (2.9 g, 43.7 mmol) in DCM (20 mL) was added TBSCl (2.6 g, 16.0 mmol) at r.t., and the reaction was stirred for 2 h. The reaction was diluted with water (50 mL) and extracted with DCM (50 mL×3). Organics were washed with brine (50 mL), dried (Na2SO4), and concentrated. Purification by silica gel chromatography (PE:EtOAc=40:1) gave 3.0 g (82%) of the title compound as a yellow oil.

Aufarbeitung

  1. extractionextracted with DCM (50 mL×3)
  2. washOrganics were washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (PE:EtOAc=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-b55e90e7c7c14deca59d8047cc7e2a90
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447046B2

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