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Sodium Chloride → Diethyl 1-methyl-5-(tetrahydropyran-2-yloxy)pentylphosphonate

HRID 2014
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2014
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].[CH2:21]([Li])CCC.CI.[Cl-].[Na+]>CCCCCC.C(OCC)(=O)C.O1CCCC1>[CH3:21][CH:12]([P:13](=[O:20])([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])[CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 19689209Diethyl 5-(tetrahydropyran-2-yloxy)pentylphosphonateHCID 178418339Butyllithium

Produkt 1

HCID 19689181Diethyl 1-methyl-5-(tetrahydropyran-2-yloxy)pentylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8058HexaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

30 g (0.097 mol) of diethyl 5-(tetrahydropyran-2-yloxy)pentylphosphonate were initially introduced into 200 ml of absolute tetrahydrofuran under an argon atmosphere, cooled to -70° C. and treated with 42.8 ml (0.107 mol) of a 2.5 molar solution of butyllithium in hexane. After addition, the solution was stirred for a further 30 minutes and 15.6 g (0.11 mol) of methyl iodide were then slowly added dropwise. The mixture was stirred at -70° C. for a further 2 hours and at room temperature for 4 hours, cautiously treated with a saturated sodium chloride solution and taken up in ethyl acetate. The organic phase was washed with water and a saturated sodium chloride solution, dried over sodium sulfate and distilled in a bulb tube.

Aufarbeitung

  1. additionAfter addition
  2. stirringThe mixture was stirred at -70° C. for a further 2 hours and at room temperature for 4 hours
  3. washThe organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  5. distillationdistilled in a bulb tube

Quellen und Nachweise

ORD-Eintrag
ord-8696035fa4f54687939bb64a88e38937
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728686

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