Iodine → Diethyl 5-iodo-2-furanphosphonate

HRID 229438

Reaktionsgleichung

Reaktionsgleichung von HRID 229438
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[P:6]([O:11][CH2:12][CH3:13])(=[O:10])[O:7][CH2:8][CH3:9].C([N-]C1CCCCC1)(C)C.[Li+].[I:25]I>C1COCC1>[I:25][C:5]1[O:1][C:2]([P:6]([O:7][CH2:8][CH3:9])(=[O:10])[O:11][CH2:12][CH3:13])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 10877271Lithium cyclohexylisopropylamideHCID 12485182Phosphonic acid, 2-furanyl-, diethyl ester

Produkt 1

HCID 22280644Diethyl 5-iodo-2-furanphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of diethyl 2-furanphosphonate (prepared as described in Step A, Example 13) (1 mmol) in 2 mL THF was cooled to −78° C. and added to a solution of lithium isopropylcyclohexylamide (LICA) (1 m mol) in 2 mL THF at −78° C. over 20 min. The resulting mixture was stirred −78° C. for 20 min and added into a solution of iodine (1 mmole) in 1 mL THF at −78° C. over 20 min. The mixture was then stirred at −78° C. for 20 min. Extraction and chromatography provided diethyl 5-iodo-2-furanphosphonate as a yellow oil.

Aufarbeitung

  1. stirringThe mixture was then stirred at −78° C. for 20 min
  2. extractionExtraction and chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7d40590dc81a476cb0dea0aa96705911
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563774B2

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