3-Chloro-2-chloromethyl-1-propene → (2-Chloromethyl-2-propenyloxymethyl)phosphonic acid diethylester

HRID 398769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 398769
[CH2:1]([O:3][P:4]([CH2:9][OH:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:11][CH2:12][C:13]([CH2:15]Cl)=[CH2:14].[I+].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1.[H-].[Na+]>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:15][C:13]([CH2:12][Cl:11])=[CH2:14])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Komponenten

7

Edukt 4

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 25517Ammonium ChlorideHCID 76513Diethyl phosphonomethanolHCID 178449043HCID 178449043, Verbindung

Produkt 1

HCID 54045084(2-Chloromethyl-2-propenyloxymethyl)phosphonic acid diethylester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 24758Sodium hydrideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a mixture of hydroxymethylphosphonic acid diethylester (0.84 g, 5 mmol), 1-chloro-2-chloromethyl-2-propene (0.95 g, 7.6 mmol) and tetrabutylammonium iodine (0.18 g, 0.5 mmol) in anhydrous tetrahydrofuran (10 ml), sodium hydride is added (0.24 g, 6 mmol 60% in oil) at 0° C. The mixture is stirred overnight at 20° C. The reaction mixture is hydrolyzed with a saturated solution of ammonium chloride, extracted with ethyl acetate and the title product is obtained by flash chromatography on silica gel (0.35 g, 27%).

Aufarbeitung

  1. additionis added (0.24 g, 6 mmol 60% in oil) at 0° C
  2. extractionextracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c4b1974d5efb4fcbb175ef143df02274
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817647

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