Tetrahydrofuran → 1,3-Bis(diethylphosphonooxy)-4-ethylbenzene

HRID 449790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449790
[O:1]1[CH2:5][CH2:4]CC1.[CH2:6]([C:8]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][C:9]=1[OH:15])[CH3:7].[H-].[Na+].[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19]>O>[CH2:21]([O:20][P:18]([O:12][C:11]1[CH:13]=[CH:14][C:8]([CH2:6][CH3:7])=[C:9]([O:15][P:18]([O:1][CH2:5][CH3:4])([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=1)([O:23][CH2:24][CH3:25])=[O:19])[CH3:22]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 179274-EthylresorcinolHCID 24758Sodium hydride

Produkt 1

HCID 545972611,3-Bis(diethylphosphonooxy)-4-ethylbenzeneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a tetrahydrofuran solution (10 ml) of 4-ethylresorcinol (691 mg), sodium hydride (60% dispersion in liquid paraffin) (440 mg) was added and stirred at 0° C. for 30 minutes. Then, diethyl chlorophosphate (1.73 ml) was added dropwise. After stirring at room temperature for 3 hours, water (10 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (10 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.43 g) was subjected to silica gel chromatography (silica gel 40 g, chloroform to chloroform:methanol=10:1), to give the title compound (2.05 g, yield: 100%) as a pale yellow oil.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionthe extraction
  3. washThen, the extract was washed with saturated brine (10 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-42cc9b0905be40cca21db77815f602f9
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486919B2

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