Tetrahydrofuran → HCID 86682690, Verbindung

HRID 449786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449786
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]([C:9]1[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][C:10]=1[OH:16])([CH3:8])[CH3:7].[H-].[Na+].[P:19](Cl)([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O>[CH2:5]([O:1][P:19]([O:13][C:12]1[CH:14]=[CH:15][C:9]([CH:6]([CH3:8])[CH3:7])=[C:10]([O:16][P:19]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:11]=1)([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C:4]1[CH:30]=[CH:31][CH:32]=[CH:2][CH:3]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 901354-IsopropylresorcinolHCID 4641201(Chloro(phenylmethoxy)phosphoryl)oxymethylbenzene

Produkt 1

HCID 86682690HCID 86682690, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a tetrahydrofuran solution (10 ml) of 4-isopropylresorcinol (466 mg), sodium hydride (60% dispersion in liquid paraffin) (269 mg) was added and stirred at 0° C. for 30 minutes. Then, dibenzyl chlorophosphate (10 w/v % solution in benzene) (20 ml) was added dropwise. After stirring at room temperature for 3 hours, water (30 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 (20 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.23 g) was subjected to silica gel chromatography (silica gel 76 g, chloroform to chloroform:methanol=70:1), to give 1,3-bis(dibenzylphosphonooxy)-4-isopropylbenzene (1.71 g, yield: 83%) as a yellow liquid.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionthe extraction
  3. washThen, the extract was washed with saturated brine (20 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-06ef22596580407d9d66f20315f33726
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486919B2

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