Ammonium Chloride → 5,5-Di[(diethoxyphosphoryl)methyl]-2,2-dimethyl-1,3-dioxane

HRID 578607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 578607
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[Na+].Br[CH2:11][C:12]1([CH2:20]Br)[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1.[Cl-].[NH4+]>C1COCC1.CN(C=O)C>[CH2:3]([O:2][P:1]([CH2:11][C:12]1([CH2:20][P:1]([O:5][CH2:6][CH3:7])([O:2][CH2:3][CH3:4])=[O:8])[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][CH2:13]1)([O:5][CH2:6][CH3:7])=[O:8])[CH3:4]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 145372285,5-Bis(bromomethyl)-2,2-dimethyl-1,3-dioxaneHCID 23684067Sodium diethyl phosphite

Produkt 1

HCID 896300935,5-Di[(diethoxyphosphoryl)methyl]-2,2-dimethyl-1,3-dioxaneAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
68 °C

Versuchsvorschrift

Sodium diethyl phosphite (63.6 g, 400 mmol, 6.0 eq.) was added to a solution of 5,5-di(bromomethyl)-2,2-dimethyl-1,3-dioxane (20.0 g, 66 mmol) in an anhydrous mixture of THF/DMF (9:1, 600 ml). The reaction mixture was stirred for 15 h at 68° C. and subsequently mixed with a saturated aqueous solution of ammonium chloride (20.0 ml) and the volatile constituents were removed in vacuo. The residue was diluted with deionized water (200 ml) and the solution formed was extracted with methylene chloride (3×200 ml). The combined organic phases were dried with anhydrous sodium sulphate and the solvent was then removed under reduced pressure. The obtained crude product was purified by flash column chromatography (eluent: ethyl acetate/methanol 9:1). 19.6 g (71% yield) of the product was obtained as a colorless oil.

Aufarbeitung

  1. customthe volatile constituents were removed in vacuo
  2. additionThe residue was diluted with deionized water (200 ml)
  3. customthe solution formed
  4. extractionwas extracted with methylene chloride (3×200 ml)
  5. dry with materialThe combined organic phases were dried with anhydrous sodium sulphate
  6. customthe solvent was then removed under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by flash column chromatography (eluent: ethyl acetate/methanol 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-e0c8aa747f3c49bfa9c9c3df46ec71e1
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040602B2

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