2,6-Lutidine → (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanol

HRID 1035549

Reaktionsgleichung

Reaktionsgleichung von HRID 1035549
[O:1]1[CH2:6][CH2:5][CH:4]([C@@H:7]([OH:10])[CH2:8][OH:9])[CH2:3][CH2:2]1.N1C(C)=CC=CC=1C.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].[NH4+].[Cl-]>C(Cl)Cl>[Si:19]([O:9][CH2:8][C@@H:7]([CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[OH:10])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Komponenten

6

Edukt 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67156576(R)-1-(Tetrahydro-2H-pyran-4-yl)ethane-1,2-diol

Produkt 1

HCID 67157049(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (1R)-1-tetrahydro-2H-pyran-4-ylethane-1,2-diol (2.40 g, 16.2 mmol) in 60 mL of CH2Cl2 was cooled to 0° C. under N2. 2,6-Lutidine (3.77 mL, 32.4 mmol) and tert-butyldimethylsilyl chloride (2.57 g, 17.0 mmol) were added and the reaction mixture was stirred and allowed to warm to ambient temperature overnight. The reaction mixture was treated with saturated aqueous NH4Cl solution and the layers were separated. The organic portion was washed successively with aqueous 3.5% NaH2PO4 solution (2×), H2O and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 20% ethyl acetate/hexanes) gave 3.29 g of (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-tetrahydro-2H-pyran-4-ylethanol as a colorless oil.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic portion was washed successively with aqueous 3.5% NaH2PO4 solution (2×), H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-adc0d31ec9c7470ebd74a4ca37ab99ea
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546383B2

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