(Trimethylsilyl)imidazole → Trimethyl{[(2s)-1,1,2-trimethyl-3-(phenylsulfonyl)propyl]oxy}silane

HRID 388731

Reaktionsgleichung

Reaktionsgleichung von HRID 388731
[CH3:1][C:2]([OH:16])([C@H:4]([CH3:15])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:3].[CH3:17][Si:18]([CH3:25])([CH3:24])N1C=CN=C1>CN(C)C=O>[CH3:17][Si:18]([CH3:25])([CH3:24])[O:16][C:2]([CH3:1])([CH3:3])[C@H:4]([CH3:15])[CH2:5][S:6]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:8])=[O:7]

Komponenten

4

Edukt 2

HCID 28925(Trimethylsilyl)imidazoleHCID 13964863HCID 13964863, Verbindung

Produkt 1

HCID 68938726Trimethyl{[(2s)-1,1,2-trimethyl-3-(phenylsulfonyl)propyl]oxy}silaneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The compound of Example 10B (0.95 g, 3.9 mmol) was dissolved in 3 mL of dimethylformamide; 1 mL of 1-(trimethylsilyl)imidazole was added, and the resultant solution was stirred overnight at ambient temperature, then heated at 80° C. for 8 hours. The crude mixture was partitioned between ethyl acetate and water; the organic phase was washed with brine and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 0% to 20% ethyl acetate in hexanes to provide the titled compound (1.18 g, 96%).

Aufarbeitung

  1. customThe crude mixture was partitioned between ethyl acetate and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by chromatography on an Analogix Intelliflash 280™
  6. washeluting with a gradient of 0% to 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8baa344f47184079aa6489b993392493
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377913B2

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