Ethylene Glycol → 2-[2-(N-allyloxycarbonyl-N-benzylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane

HRID 1029661

Reaktionsgleichung

Reaktionsgleichung von HRID 1029661
[CH2:1]([O:4][C:5]([N:7]([CH2:15][CH:16]([OH:23])[C:17]#[C:18][Si](C)(C)C)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH:2]=[CH2:3].[CH2:24]([OH:27])[CH2:25][OH:26].O1CCCC1.C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Hg+2]>[CH2:1]([O:4][C:5]([N:7]([CH2:15][CH:16]([C:17]1([CH3:18])[O:27][CH2:24][CH2:25][O:26]1)[OH:23])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])[CH:2]=[CH2:3]

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 15117298HCID 15117298, Verbindung

Produkt 1

HCID 151172992-[2-(N-allyloxycarbonyl-N-benzylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24544Mercuric sulfateKatalysatorHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Mercury(II) sulfate (3.55 g) was added to a solution of 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol (19.75 g) in a mixture of sulfuric acid (0.15 ml), ethylene glycol (60 ml), and tetrahydrofuran (120 ml). The mixture was stirred at 30°~40° C. for 35 hours. Sodium hydrogen carbonate (1 g) was added to the mixture and the mixture was stirred at 30°~40° C. for one hour. An insoluble material was filtered off and the filtrate was concentrated under reduced pressure to give a syrup. A solution of the syrup in ethyl acetate (250 ml) was washed with water (150 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give an oil. The oil was subjected to a column chromatography on silica gel (400 g) and eluted with a mixture of hexane and ethyl acetate (5:5, V/V) to give 2-[2-(N-allyloxycarbonyl-N-benzylamino)-1-hydroxyethyl]-2-methyl-1,3-dioxolane (11.6 g) as a syrup.

Aufarbeitung

  1. stirringthe mixture was stirred at 30°~40° C. for one hour
  2. filtrationAn insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give a syrup
  5. washA solution of the syrup in ethyl acetate (250 ml) was washed with water (150 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. washeluted with a mixture of hexane and ethyl acetate (5:5, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-42f6adafc374424eb09d54359c8aa7e8
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05102877

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