Imidazole → ethyl (R)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

HRID 1901205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1901205
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:9]([O:19][CH2:20][CH3:21])(=[O:18])[C@@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11].N1C=CN=C1>CN(C)C=O>[Si:1]([O:11][C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([O:19][CH2:20][CH3:21])=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6951556(-)-Ethyl mandelate

Produkt 1

HCID 53734821ethyl (R)-alpha-(t-butyldimethylsilyloxy)-alpha-phenylacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of 31.4 g of t-butyldimethylsilyl chloride in 200 ml of dimethylformamide was added dropwise to a solution of 25 g of ethyl (R)-(-)-mandelate and 28.4 g of imidazole in 600 ml of anhydrous dimethylformamide, and the resulting mixture was stirred overnight at 40° C. The dimethylformamide solvent was then removed by distillation under reduced pressure, and the residue was mixed with water and then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:10 by volume mixture of ethyl acetate and hexane as the eluent. The title compound was obtained as a liquid, boiling at 129° C./3.5 mmHg (466 Pa) by distillation in vacuo.

Aufarbeitung

  1. customThe dimethylformamide solvent was then removed by distillation under reduced pressure
  2. additionthe residue was mixed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was then removed by distillation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-9f1b5efd81c34e09a0c6950347b0e3af
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576340

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