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

HRID 20493

Reaktionsgleichung

Reaktionsgleichung von HRID 20493
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([OH:13])[C@H:10]([OH:12])[CH3:11].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OCC)C.O>[Si:1]([O:13][CH2:9][C@H:10]([OH:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 259994R-(-)-1,2-Propanediol

Produkt 1

HCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-olAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl(dimethyl)silyl chloride (5.90 g, 39-5 mmol) was added to a solution of (2R)-propane-1,2-diol (3.00 g, 39.5 mmol) in DCM (100 mL) followed by diisopropylethylamine (7.10 g, 55.3 mmol) and the reaction was stirred under argon for 72 h. The reaction was diluted with diethyl ether (500 mL) and water (140 mL) and the organic layer was separated then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 1:15 to 1:10 ethyl acetate:hexane, afforded the title compound as a colourless oil (6.00 g, 80%).

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by column chromatography
  6. washeluting with 1:15 to 1:10 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-928e514db4e94bc4bc89503262906d42
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745475B2

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