3-(Chloromethyl)pyridine hydrochloride → 3-(Diethoxyphosphorylmethyl)pyridine

HRID 52168

Reaktionsgleichung

Reaktionsgleichung von HRID 52168
C([O-])(O)=O.[Na+].Cl.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13]Cl)[CH:8]=1.[CH2:15]([O:17][P:18]([O:22]CC)[O:19][CH2:20][CH3:21])[CH3:16]>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][P:18](=[O:22])([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16])[CH:8]=1

Komponenten

4

Edukt 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 31215Triethyl phosphiteHCID 516892Sodium Bicarbonate

Produkt 1

HCID 104626053-(Diethoxyphosphorylmethyl)pyridineAusbeute 26,2 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of saturated NaHCO3 was added 3-picolyl chloride hydrochloride (8.2 g, 50 mmol). After gas evolution ended, the mixture was extracted with CH2Cl2. The organic phase was dried (MgSO4) and concentrated in vacuo. To the resulting residue was added triethylphosphite (8.3 g, 50 mmol) and the neat mixture was stirred and heated at 85° C. overnight. The mixture was cooled and purified by flash column chromotography on silica gel eluting with 5% MeOH--CH2Cl2 to afford 3.0 g of diethyl 3-pyridylmethylphosphonate as a yellow oil.

Aufarbeitung

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. temperatureThe mixture was cooled
  5. custompurified by flash column chromotography on silica gel eluting with 5% MeOH

Quellen und Nachweise

ORD-Eintrag
ord-3480f0481a594e518e4e31c7f928693f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616596

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