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

HRID 2014

Reaktionsgleichung

[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

Komponenten

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

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