Imidazole → (2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-ol

HRID 493371

Reaktionsgleichung

Reaktionsgleichung von HRID 493371
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:9]([OH:13])[C@H:10]([OH:12])[CH3:11].N1C=CN=C1>ClCCl>[O:13]([CH2:9][C@H:10]([OH:12])[CH3:11])[Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 259994R-(-)-1,2-Propanediol

Produkt 1

HCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-olAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of tert-butyldimethylchlorosilane (9.9 g, 65.7 mmol) in dichloromethane was added dropwise to a solution of (R)-(−)-1,2-propanediol (5 g, 65.7 mmol) and imidazole (4.47 g, 65.7 mmol) in anhydrous dichloromethane at 0° C. The reaction mixture was stirred at 0° C. for 30 min before dilution with dichloromethane. The solution was washed with water three times followed by the addition of brine. The organic layer was separated, dried through a MgSO4 pad and concentrated under reduced pressure to afford 12.0 g (96%) of (2R)-1-(tert-Butyldimethylsiloxy)propan-2-ol.

Aufarbeitung

  1. washThe solution was washed with water three times
  2. additionfollowed by the addition of brine
  3. customThe organic layer was separated
  4. dry with materialdried through a MgSO4 pad
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7aeeb593719a4b0ea9601e19858f3838
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534813B2

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