tert-Butyldimethylsilyl chloride → 1-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-ol

HRID 1754444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754444
[CH3:1][C:2]([OH:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:8]([Si:11]([CH3:13])([CH3:12])[O:4][CH2:3][C:2]([CH3:5])([OH:6])[CH3:1])([CH3:10])([CH3:9])[CH3:7]

Komponenten

5

Edukt 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 684102-Methylpropane-1,2-diol

Produkt 1

HCID 189346221-((Tert-butyldimethylsilyl)oxy)-2-methylpropan-2-olAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Methylpropane-1,2-diol (1.08 g, 12.0 mmol, 1.0 equiv) in DCM (40 mL) under argon was cooled to 0° C. TEA (2.50 mL, 18.0 mmol, 1.5 equiv), DMAP (75.0 mg, 0.600 mmol, 0.05 equiv), and TBSCl (2.00 g, 13.2 mmol, 1.1 equiv) were added sequentially, and the reaction was allowed to warm up to ambient temperature overnight. Complete conversion of reactant to product was confirmed by TLC eluted with EtOAc and visualized with KMnO4. The solvent was removed in vacuo, and the residue was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc 2×, and the combined organics were dried with Na2SO4, filtered, and concentrated to provide 1-(tertbutyldimethylsilyloxy)-2-methylpropan-2-ol (2.05 g, 84%) as a light brown oil that was used without further purification.

Aufarbeitung

  1. washeluted with EtOAc
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc 2×
  5. dry with materialthe combined organics were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f27d3a210ee475cae39ddb703ec53ff
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169249B2

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