Imidazole → 1-Butanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-

HRID 512881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512881
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C.C(OCC)C>[Si:17]([O:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 109758164-Hydroxy-1-phenylbutan-1-one

Produkt 1

HCID 110657931-Butanone, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-phenyl-Ausbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-1-phenyl-butan-1-one (3.29 g, 20 mmol) in DMF (20 mL) was added tert-butylchlorodimethyl-silane (4.5 g, 30 mmol) and imidazole (4.1 g, 60 mmol). After stirring at room temperature for 14 hours, the reaction mixture was diluted with diethyl ether (150 mL) and washed with 1M HCl (2×70 mL), water (2×70 mL) and brine (100 mL). The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (6% ethyl acetate in hexanes) to provide the product (5 g, 90%) as a colorless oil.

Aufarbeitung

  1. washwashed with 1M HCl (2×70 mL), water (2×70 mL) and brine (100 mL)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (6% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-863a5d84014943dca0df2cf87b32d812
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102639B2

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