Imidazole → 3-(Tert-butyldimethylsilyloxy)propiophenone

HRID 1614228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614228
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].N1C=CN=C1>CN(C)C=O>[Si:1]([O:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 569605Hydroxypropiophenone

Produkt 1

HCID 135233483-(Tert-butyldimethylsilyloxy)propiophenoneAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Tert-butyldimethylsilyl chloride (22.5 g) was added to a mixture of 3-hydroxypropiophenone (18.7 g), imidazole (21.3 g) and dimethylformamide (100 ml) and the solution was stirred at ambient temperature for 6 hours. The mixture was evaporated and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with an aqueous sodium chloride solution, dried (Na2SO4) and evaporated. Petrol (b.p. 60°-80° C., 250 ml) was added to the residue, the resulting mixture was filtered and the filtrate was evaporated to give 3-(tert-butyldimethylsilyloxy)propiophenone as a pale yellow oil (31 g) which was used without further purification.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with an aqueous sodium chloride solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. additionPetrol (b.p. 60°-80° C., 250 ml) was added to the residue
  8. filtrationthe resulting mixture was filtered
  9. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-37872556cdf245069fe0dceeec8cd989
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196422

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