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Ethyl Methanesulfonate → Ethyl (diethoxyphosphoryl)methanesulfonate

HRID 129783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 129783
[CH3:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3].[Li]CCCC.[P:13](Cl)([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:16]([O:15][P:13]([CH2:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3])([O:18][CH2:19][CH3:20])=[O:14])[CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6113Ethyl MethanesulfonateHCID 13139Diethyl chlorophosphateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 10934205Ethyl (diethoxyphosphoryl)methanesulfonateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of ethyl methanesulfonate (4.27 mL, 40.3 mmol) in 100 mL of dry THF was treated at -78° C. with 19.3 mL (44.4 mmol) of n-BuLi in hexane. After 15 min. diethyl chlorophosphate (3.30 ml, 22.2 mmol) was added. The solution was kept at -78° C. for 0.5 h and allowed to stay at -50° C. for 1 h. Saturated ammonium chloride (75 mL) was added to the solution and the mixture warmed to room temperature. The mixture was concentrated (THF removed), diluted with water and extracted with methylene chloride (3×70 mL). The combined organic fractions were dried (MgSO4), concentrated and purified by distillation to yield 3.86 g (70%) of title compound.

Aufarbeitung

  1. waitto stay at -50° C. for 1 h
  2. concentrationThe mixture was concentrated
  3. custom(THF removed)
  4. additiondiluted with water
  5. extractionextracted with methylene chloride (3×70 mL)
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. concentrationconcentrated
  8. distillationpurified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-33529eec5d4f4ebf99ed1915cc5ec481
Quelldatensatz
uspto-grants-1995_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05470845

Notizen zur Reaktion

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