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Imidazole → 4-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-ol

HRID 1968913
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1968913
[CH3:1][C:2]([CH3:8])([CH2:5][CH2:6][OH:7])[CH2:3][OH:4].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1COCC1>[Si:14]([O:7][CH2:6][CH2:5][C:2]([CH3:8])([CH3:1])[CH2:3][OH:4])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]
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Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 108878792,2-Dimethylbutane-1,4-diol

Produkt 1

HCID 197346474-{[Tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylbutan-1-olAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product from Example 9A (0.80 g, 6.8 mmol) and imidazole (0.462 g) in THF (8.0 mL) at room temperature was added tert-butyldimethylsilyl chloride (1.02 g), and the solution was stirred for 16 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography on silica gel, eluting with a gradient starting with 33% hexanes in chloroform and ending with 25% ethyl acetate in chloroform, to give the title compound (1.153 g, 73%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe organic was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with a gradient

Quellen und Nachweise

ORD-Eintrag
ord-3b84396153d94f2faa1e0b32ec4fb27d
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426388B2

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