Acetic Acid → 1-(4-Dimethylphosphonomethoxytetrahydro-2-furyl)thymine

HRID 2293719

Reaktionsgleichung

Reaktionsgleichung von HRID 2293719
CO[CH:3]1[O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][CH2:4]1.CO[P:19]([O:23][CH3:24])([O:21][CH3:22])=[O:20].[C:25](O)(=[O:27])C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:24][O:23][P:19]([CH2:25][O:27][CH:4]1[CH2:3][O:7][CH:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5]1)([O:21][CH3:22])=[O:20]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10541Trimethyl PhosphateHCID 521998p-Toluenesulfonic acid monohydrateHCID 189394271-(5-Methoxytetrahydro-2-furyl)thymine

Produkt 1

HCID 540926261-(4-Dimethylphosphonomethoxytetrahydro-2-furyl)thymine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-(5-methoxytetrahydro-2-furyl)thymine (5.2 g, 23 mmol) and dimethylphosphonomethanol (6.5 g, 44 mmol) in toluene was added acetic acid (5 mL) and p-toluenesulfonic acid monohydrate (500 mg, 2.6 mmol). The solution was heated at 100° C. for 2 hr and the resulting insoluble solid was removed by suction filtration. After removal of the solvent under reduced pressure, the residual oil was chromatographed on silica gel using CH2Cl2 /5% MeOH as eluent to give the title compound as a cis/trans mixture (6:4): yield 5.0 g (60%).

Aufarbeitung

  1. customthe resulting insoluble solid was removed by suction filtration
  2. customAfter removal of the solvent under reduced pressure
  3. customthe residual oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5d083594f26649d3af6216a68059bd2b
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686611

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